#1009: Persistence is grossly overrated in dating and romance.

Dear Captain,

I am a man and I have a problem: I’m a creep.

I’m 30 years old, and I haven’t had a whole lot of romantic experience. I’ve been shy my whole life and dealing with anxiety and depression since my teen years, so I haven’t put myself out there as much as I could have, and haven’t had the self-confidence to be a good prospect in the past.  My social skills have been getting better, and I’m getting treatment for my mental health issues.  I think I’m capable of dating now, and I’ve met a few interesting women to connect with in the last year or so.  These days, I even manage to gather up my courage and ask them out/confess my feelings.  However, I never to seem to get a straight “yes” or a “no”, and I end up responding in a bad way.  Some examples:

I met a friend-of-a-friend a few times before, and we had flirted with each other, so I was feeling confident about our connection.  Our group went to a party a while back, and I ended up asking to kiss her when we alone at one point.  She said “I don’t know” and it looked like she was nervous and didn’t know what to do.  I backed off physically, but I pressed the point: mostly questions in the “why not?” vein.  We parted without incident, but met back up at the end of the party (the group was riding back together).   For some reason, I tried to flirt some more, and I just ended up creeping her out.  I’ve had enough self-awareness to keep my distance ever since, though the damage has already been done.

Another scenario: I saw a woman on a regular basis at an activity.  I liked her, and told her so one day.  Confronted with the news, she became very awkward and didn’t give a clear verbal response (“oh…uh…”).  We ended up having a good conversation (about
everything else), but my declaration was left hanging.  Before I saw her again, I e-mailed her to ask to talk again—I had been flogging myself for not knowing what to say.  Her response was a clear “no”, and it was obvious that my e-mail had been unwelcome.  I was glad to get the straight-up answer, but I had to push her boundaries to get it.

There have also been a couple of recent instances where I’ve asked a woman out and didn’t take her “I can’t make it” as an “I don’t want to”, and have ended up pestering them again.

It’s clear that I’m establishing a disturbing pattern: I get interested in a woman; I make a move; she gives a non-committal response; I don’t take it as the brush-off it is and end up making unwelcome contact (i.e. asking for a date again, “but why?”, continuing to flirt beyond its welcome).  I know intellectually that getting a non-answer in these situations means “no”.  It’s also clear in retrospect that I should’ve just backed off in these cases, but I seem to panic in the moment and not act on that knowledge.  Through some combination of wishful thinking, inexperience and brain weasels, I’m pushing women’s boundaries and acting like a creep.

Any thoughts, Cap’n?  I feel so guilty about these instances, and I’ve reaped the personal consequences—burnt bridges and cold shoulders—but I’m still not getting it right.  How do I remember to bow out gracefully in such a moment?

– Don’t Wanna Be A Creep

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Image description: A giant panda sits in a pink rocking chair. It covers its face and slumps down in a convincing imitations of human shame.

Hey Friend, I see you and I used to be you. No, really. Lest we forget, I once left a multi-page letter on someone’s pillow in the bedroom where they sleep.

Media portrayals of romantic pursuit reward persistence. This is doing you (and many, many, many other people) a grave disservice.

You’re not doing anything wrong by asking people on dates, asking them to kiss them, or telling them you like them. There are exceptions – I think teachers hitting on their students is always pretty creepy, for instance, and your cute barista smiles that way at everyone because she is trapped at work and capitalism demands her emotional labor – but feeling attracted to someone and asking them about it isn’t creepy. Also, you are asking, not doing that “making a move” thing in movies where men grab women and mash their faces together that is romantic in fantasy and consensually in established “grabbing” relationships but not actually in real life. So, you haven’t crossed all the way over into creepy. It’s not too late!

So let’s work on your follow-up. Next time you feel that spark of interest in somebody, keep doing what you’re doing and ask. You’re not naturally smooth, so don’t try to become smooth at this. Just be yourself and be direct.

You:I’d really love to kiss you/take you on a date/get to know you better.”

Nice lady:Hrm…I don’t know about that.”  

You:Ok! I hope you don’t mind me asking. If you ever change your mind, let me know.

Your “creep” self-label is probably 99% you being really hard on yourself, but I sense a little resentment or confusion on your part about not getting “clearer” answers. This is actually pretty simple to handle going forward. Treat anything that is not “Yes!!!!!” like “No.” Can’t make it = no. Let me think about it = no. I don’t know = no. Not now = no. You don’t need to push for a clearer answer or settle the question or codify the rejection. Did she say “Yes, I’d love to!?” No? Then drop it. Stop auditing her answers for the yes.

Rejection doesn’t mean you have to hide your face in shame forever or get all weird and Firthy about it, though! Go back to being polite and friendly and never mention it again until or unless she does. You can show that you are safe and trustworthy by being safe and trustworthy. If she flirts with you, it’s okay to flirt back, but don’t renew the request for a date or a kiss. Let her come to you with that. If she doesn’t, that’s your answer.

If it gets too uncomfortable for you to be in limbo with someone, it’s okay for you to pull back on the interaction. Just because you were comfortable with it once upon a time doesn’t mean you have to be comfortable with it when your feelings are hurt.

Women don’t forget when dudes ask them out. We don’t need reminders. If a lady really is on the fence about the whole thing and her “hrmmm…interesting” reaction was a genuine “I don’t know,” she is perfectly capable of coming and finding you later and asking “Is that offer still good?”  I once suddenly needed to check my mail in another part of campus at two in the morning so I could keep walking in tandem with the gentleman I was walking home from a party with so we could mutually and consensually maneuver ourselves onto the Couch of Let’s Put On Some Portishead Now That I Have My Very Important Postal Material That Could Not Wait For Daylight. A woman who genuinely wants to look at your etchings will find a way to ask you about them.

You say you are shy and you don’t have a lot of confidence. This is how you build/practice/get confidence: You say your piece, you let the other person make a decision, and you trust that once in a while someone will decide you are worth risking an awkward conversation for. Until that happens, you trust in yourself, in your own worth and good and valiant heart, and pour your love and your time into your friendships, your family, your work, your education, your hobbies, and your community. Live to date again another day.

Another suggestion? Make your date requests more specific. You say you aren’t getting clear yes or no answers, so, make your requests for dates or whatever easier to say a clear yes or no to. “Would you like to be my date to this comedy show on Thursday?” vs. “Can I take you out sometime?”

If the person says “No thanks” that’s your answer!

If someone says no to Thursday, specifically, but yes to the idea, you are cleared to ask again, one time. If it gets super-hard to make plans and it feels like there is never the right time, 1) Stop:I’d still really love to get together, why don’t you call me when your schedule opens up and we’ll figure something out?2) Drop (the subject) and 3) Roll your attention somewhere else.

Maybe someday I’ll stop gushing about Mr. Awkward but today is not that day. He asked me out on Ok Cupid. I said “Yes, but I am sick and busy, can we try this in a couple of weeks?” He said “Sure” and (this is key) then he left me alone. He assumed he was never going to hear from me again and moved on with his life. In a couple of weeks, I got in touch with him and asked him on a date. What if I had never written to him? We might never have met. What if he had written to me repeatedly to get me to go out with him? We also might never have met. Read on for a cautionary tale.

Pickup Artists and other dregs at the bottom of the dating pool talk about something called the “shit test” – where women say no to an early request to test to see if the guy will persist, and they encourage you to push back on this early no. One of my early dating tests that I didn’t realize was a test at the time is the “Hey will this stranger take no for an answer because I kind a need to know” test. I once mentioned to a dude from an online dating site that I would call him over the weekend to confirm plans for a date. Some actual big deal life stuff came up and I forgot to call him. At precisely 9:00 am Monday morning I got a text that said “You didn’t call. 😦” and I had a strangely visceral “Nope!!!!” reaction to reading it, like, ugh, this is already too much work. I was like “Oops, I had some family stuff, sorry” and He was like “My time is very valuable, I don’t like reserving time in my schedule for flakes” and I was like “I hear that, okay, sorry again, let’s skip getting ice cream after all, good luck out there” and then












I get from the interactions that he’d been really looking forward to the date and that I hurt his feelings by being less interested. It was probably never gonna happen after that initial 😦 but it was definitely not gonna happen after “Why did you say you’d go out with me if you didn’t intend to follow through?” He was cute and smart and we liked the same geeky stuff but he put my shoulders up around my ears and once they went up they weren’t coming down.

Don’t be Sad Emoji Guy. Persistence is overrated. Pushy people get my back up and if you’re a shy guy who is not very experienced at dating your best dating pool is going to be your fellow shy people who are not so experienced at dating and they are not necessarily going to enjoy feeling hunted by you.


  • Stop asking for women’s phone numbers or emails when you meet them in bars or group settings. “I’d love to chat with you more, can I give you my info?” Hand them a card (or literally a scrap of paper with your name and a way to contact you on it, please do not overthink this)Remove the anxiety of “when do I call/should I call/how do I call/what do I say when I call” from your life completely right now. Change up the idea of pursuit in romance. Whenever I give this advice some dude points out “But he won’t get any calls that way” and it’s like “Maybe not! But if someone does call you’ll know she really wanted to, and in the meantime you made the world suck less by not pressuring women for contact info.” If she loses it, so what. If she doesn’t like your font, so what. The whole point is to stop worrying about it once you give her your info instead of pressuring her for hers. If she met you and she really liked you, chances are she’ll tuck it in a safe place.
  • Don’t be Social Media Hover Guy. Let’s be clear, I would always, always Google potential dates and get an idea of their general online vibe and how well it matched up with what they’d told me, and I think everyone should do this (It’s one way to figure out early on if someone is a Nazi, for instance!) And we’re only human, and photos of our crushes are fascinating. However, when you are trying to connect with someone, don’t monitor their feeds and mention everything they’ve ever done back to them, don’t become the person that “likes” every single thing they say (Really you “like” when I wished my Mom a happy birthday 2 months ago?), DON’T click “like” on all their old pictures. It’s about as subtle as skywriting, and it just feels, as you said, creepy to know someone is monitoring you to that extent.
  • Watch for reciprocity. If you are sending 5 emails or texts for every 1 of hers, and yours are like Tolstoy wrote them where she is more Dorothy Parker, ease off a bit.
  • Read more books by women and take in art by women. If you already read books by women, great? Keep doing that. Ashley C. Ford just had a great Twitter thread on books by black women people are reading & excited to read if you need to refresh your list. Watch movies by women. Listen to music made by women. You want to love women and be with women? Recognize the ways that the world is out of balance for us and look for stories and creative works that address that.
  • Be politically active about things that are important to women. In the spring it was reported that women are making 86% of the phone calls to resist the current administration’s policies. Do you want to be with women, sleep with women, love women? Have you noticed we’re kinda busy right now? Love us by doing your part so that we can survive and thrive and have some free time to think about dating a nice fellow like you. I will stop adding this advice to dating threads when I see that number move to 50%.

You can’t logick someone into loving you. There is no series of perfectly executed steps that get you there. You’ve reached this moment of self-awareness about what you’re doing and it doesn’t feel good but growth never does.

This is all very fixable and I wish you luck in fixing it.

Captain Awkward


Comments closed as of 10:17 pm.

189 thoughts on “#1009: Persistence is grossly overrated in dating and romance.

  1. A thing I find useful for remembering to let go of lukewarm responses as potential yeses is Mark Manson’s piece on accepting no less than a “fuck yes!”

    If someone isn’t sure whether they want to give it a go with you, you probably shouldn’t be that excited about the kind of date their lukewarmness could produce anyway.

    1. Yes! My first thought as I read the letter was “anything but an enthusiastic yes is a pretty clear no”.

      BTW back in my single days, I discovered the hard way that the male version of this is to say “I’ll let you know” or “I’ll have to get back to you”. And that “guys love it when women ask them out” was really not so true.

      1. In my experience, (many but not all) guys are flattered when women go against “traditional” social norms and ask them out. They may even go out on a date for similar reasons that a woman who’s not super into someone would: curiosity, boredom, politeness, not wanting to hurt someone, feeling super lonely. But the simple act of asking a man out as a woman doesn’t change his attraction level to you or your baseline compatibility!

        People saying “men love it when women ask them out” are often kind of…confused by what matters in a relationship. One date with a person of questionable willingness and interest level is not success.

      2. I find that what a lot of men really mean when they say, “I’d love it if women asked me out” is “I’d love it if women I’ve already decided I’m attracted to read my mind and asked me out”.

        1. This.

          Also, this isn’t something that can realistically be gender-flipped, since MOST of the time straight men don’t get asked out and therefore do not get the experience most women have of being asked on dates – which includes being bugged while busy, wildly inappropriate asks (“dude you’re her dad’s age”), harassment, and so on, and is not limited to “being asked by guys she’s interested in” – but the last one is the only one that comes to mind.

          1. Oh amen to the dad generation thing. One former suitor is the dad of my childhood bestie and is my little nieces grandfather. The invitation came after he told his ex wife “I’m going to get myself a young woman!” Like…fetching a can of beans. While my date site inbox was exclusively full of dad types blind to my stated age range.

      3. In my experience, guys love it when women they are attracted to ask them out. They don’t seem so keen when it’s women they’re not interested in. Which, fair enough. I feel the same way. But then it would cheese me that those men would complain about not getting dates because “women aren’t interested in me!” I’m sorry. I WAS interested in you, and I said so. Now I am firmly not.

    2. I use this as well. Last time I went fishing online I met a lot of “yay, you’re a girl” and that just doesn’t cut it for me anymore. They always tended to take my uk size 18 as a “I can live with it” and not a “those curves are lush” too. So I stopped going for the tepid guys and got only into the scorching hot fuck yes guys. I found someone who makes my everything tingle and that’s because I dared to go big for once.

    3. Thanks for introducing me to that blog – great stuff on there.

      On a tangent, it’s very, very interesting that his scripts are more assertiveness-veering-into-aggressiveness compared to the Captain’s, or Carolyn Hax’s, or Ask A Manager’s scripts (who are all women) – I’m thinking specifically of the Boundaries post. I’m a woman and I tend to be very diplomatic unless I get push back – then I end up veering into aggressive territory a la Mark’s scripts. I’m not convinced borderline aggressiveness is the *always* the right way to go, but especially with men it often sure does work better than softer scripts.

  2. The Captain’s advice is spot on! I have to give kudos to the LW though – he knows he has a problem and is asking for help. Realizing you are coming across as creepy is the first step towards learning how to stop that behavior. If a woman gives you anything other than an enthusiastic “yes!” it’s time to back off.

  3. Hey LW! Good on you for recognizing that there is a problem and the problem is your behavior, and good on you for writing in for help. You’re already way ahead of a lot of sad single dudes out there, just by doing this.

    I really understand the feeling of making a terrible “panic” call in the moment and then looking back and going “wtf why did I think that was the right thing to do?” Something that might help is to take a step back and not let yourself make a followup in the moment you feel the urge to do so. Impose a mandatory waiting period on yourself long enough to get out of that awkward “panic” place and double-check whether you really need clarity or just want it.

    There’s a saying I love for social interaction, and it’s this: “Practice doesn’t make perfect. Practice makes permanent.” The more you practice not saying this stuff, the more you can get in front of your impulses and moderate them, the more natural it will get to do so.

    But – for real – you’re on the right track here. You know there’s a problem, you’ve correctly identified it, and now it’s just how to game yourself to keep those weird in-the-moment impulses in check.

    1. Great point about putting a pause on the instinct to respond in a way you might regret. Making it a rule to wait to bypass the urge to push/persist seems like a good way to avoid doing something you might regret later.

    2. Yes to this!

      I have done some pushy problematic things…one time I was really into this guy I had gone on two or so dates-ish (aka drunkenly made out with) and then he said he was too busy and too stressed right now to have this conversation but we could talk in a couple of weeks. I waited…for like 2 months. And then since we worked in the same arty studio building, and we both would be there late sometimes. I interrupted him once at like 2 am reminding him of his promise to follow up and it had been so long and “why?” Spoiler alert: I did not get the guy.

      In my case I did try and wait but once I hit my critical agony point of not-knowing, I had to force the question that moment regardless of the hour.

      Delaying my knee-jerk reaction has helped. My anxiety and desire does not entitle me to a clear answer anytime anywhere. If I let time pass I tend to calm the worst of my stress and also realize it is likely a NO and this is my own shit to handle as it were.

    1. For real. You aren’t owed an explanation. Her “NO” in whatever active or passive form she gives is enough.

  4. Great advice as always.

    Don’t Wanna Be A Creep, I wonder if you’re plagued by the “well… but what if…?” like I used to be. Well, she was noncommittal and vague so that’s probably a no, but what if I wasn’t actually that clear and she’d be less vague about yes/no if I reiterated my interest? I know I definitely was when I was in the dating pool.

    I think one great thing to remember is that you’re 30. I assume the women you’re interested in are likely around that age as well, and one of the benefits of being not-essentially-a-teenager is that by and large we all get a little bit better at knowing our own minds and trusting that other people know their own minds as well. Obviously not everyone is super great about being straightforward by the time they’re 30, but I think it’s safe to trust that the women you’re interested in are probably pretty okay at saying nearly what they mean. Or at least trust that they feel marginally confident in pursuing the people and things they want to pursue.

    You don’t need to play the “well, but what if” game. Chances are everything the Captain says is true. They won’t forget you asked them out, and if they want to go on a date with you in the future they will come find you.

    (I don’t mean to imply that ~young people~ are always wishy washy or unsure, or incapable of knowing what they want, or never say what they mean. We should always take people at their word [and reconcile that with their actions]. I just think that a lot of us are/were less sure of how to go about Peopling at that age and therefore it was much harder to resist the “well, but what if” urge. When you’re unsure of yourself, how can you be sure other people are sure of themselves?)

  5. my only comments are
    – it sounds like you are doing OK on the confidence thing so far! You self describe as shy but you’re going out on a limb and asking these people out anyway – that’s cool! Good job.

    – if you REALLY know that you should back off but you just word vomit in the moment, try role play. Like, not sexy role play, like business school role play (to bring it back to Pride & Prejudice, remember that scene in the 2005 film where Bingley practices his proposal at Darcy? that). Find a good friend to reject you, say “hey would you like to go see a movie this weekend?” and have them say “No. Uh. Maybe. I’ll have to think about it” while you say “oh, ok, let me know what you decide” and then change the subject. Practice makes perfect

    – personally I find ‘cards’ in a social situation a total douchebag move. In my circle they scream “I am a man in high speed finance/project management/law and I think I am way cooler than you do”. Maybe you’ve got different social circles though where this is appropriate? Maybe instead say they can find you on Facebook, or scribble down your twitter handle on the back of a receipt.

    1. At the Awkward Singles Meetups we did for a while we made cards, where you could scribble your info and indicate if you were seeking a friend-hangout or a date-hangout. I should create stationery along these lines.

      1. I think messaging on social media is a good medium for giving out your number. But it involves getting an in-person OK first imo. “Are you on facebook? Can I message you sometime”

        1. I would say whatever the medium is, the important thing is putting it 100% in the other person’s court and not asking them for any of their contact info. Once I’m tracking you down on social media and messaging you, it’s not all in your court, so a better thing would be “I’m x-name on social media if you ever want to find me, thanks for the conversation” and then leave. Let the other person do 100% of the work of getting in touch after that initial moment of meeting, give them a way to get in touch with you, don’t try to tease out how to get in touch with them.

      2. That’s a great idea! I have graphic design skillz (and software) that I would be happy to donate to this cause!

      3. My “card” is one of those self-inking rubber stamps that have moveable type. They’re usually found in offices where they have to write the same. blessed. thing. fifty times a day.

        It has my email address and two most active social media presences; I stamp it on 3×2.5″ note cards or small bits of paper. It doesn’t look like something I went to any great expense to get (though the stamps are not super cheap). I don’t have to have a ton of them on hand at any given time, and I can re-do it any time there’s a major change with no further real expense.

        It *doesn’t* have my phone number on it, because I want it to be something I’m comfortable giving out, but there’s room to write stuff on there if I want to add it, or the event and date, or something.

        So far it’s struck the right balance between easy to create and cute/homemade, if the “Oh wow this is so neat!” reactions from friendly acquaintances are to be relied on.

    2. Seconding ninja o on the cards thing! Where I live, I get inundated with business cards any time I am at an event. There is a high possibility that LW’s card will get lost in the sea of other cards.

      1. And you know what? As a result the Letter Writer might not meet you again. So what?

        More important than finding The Perfect Way is finding a thing that’s easy for him. If the LW hands out a card, and a woman thinks the card thing is cheesy? Who cares? It’s better than bugging her for her info. The point isn’t “use a card” or “don’t use a card” the point is find a way to put the communication ball in the woman’s court and then walk away with a “if it happens, it will happen, if it doesn’t, fine” attitude, not to give the letter writer something else to worry about and overthink. If she likes you, a card won’t kill it. If she doesn’t like you anyway, a card won’t matter.

        1. Word. Also, if the LW is doing online dating, I have really really appreciated it when considerate dudes said something like ‘I hope we can meet up again!’ And either asked me to follow up with them via the app/site or whatever we had been using (text, email, whatever) or followed up later wih me through the app instead of asking for a ‘yes’ or my phone number then and there.

        2. Put this together with the Captain’s very powerful point that women won’t forget if they’re interested. They will act, and think, on that interest.

          If she thought you were kind of fun, and you hand her a card, she is absolutely going to view that through the “he’s sort of neat” filter, and it will be a Cool Thing instead of an Unattractive Thing.

          If she thought you were neat, it won’t matter that she was inundated with other people’s business cards; she’ll put yours in the OTHER pocket. And remember you later.

          1. Yes, this. If I want what the person is selling (whether that’s friendship, romance, a networking connection, or actual non-metaphorical selling a product), then I will store or mark that card in a way that I can find it again later. If I allow it to get lost/buried, it’s because I didn’t have a strong “yes” reaction, and as noted by several people above–you don’t want someone who’s just “meh” about going on a date with you!

        3. I agree…if a person wants to call, they’ll hang on to that card/paper/napkin, etc. I’ve cleaned out my purse searching for that slip of paper given to me by another person. Once a mom at my kids school gave me her number with a breezy, “call me sometime! we should hang out.” As a person who had few friends at the time, this was a welcome thing. I ended up misplacing the number and went on a mad search through every piece of clothing, my kitchen table, my desk, and then my purse (where I found it jammed in a corner of the bottom of the bag!). My family thought I was acting like a weirdo but I didn’t care. The mom and I hung out a few times. We’re not close, but friendly…and I was introduced to three other women through her that I clicked right away with. 🙂

        4. True story: One of my lovely–awkward, nerdy, kind of shy–partners gave me a business card after sex.

          I was a little agahst, it was a ridiculous, and I have given him no end of shit about it since. I have told this story to many friends, and all agree that the image they have of the type of person who gives a woman a business card right after you have sex with them is “majorly douchy finance or management consulting dudebro” which is the polar opposite of my partner, which is why it’s so endearingly funny.

          The point of this story isn’t whether or not you should give someone a card (for what it’s worth, I think the captain’s advice is solid but think ‘written on a piece of paper’ has a better vibe than ‘actual business card’). The point is we’ve been together nearly two years.

          The point is I actually liked his face so it didn’t matter it wasn’t perfectly smooth. Because I actually liked him, I would have called him back any way he’d shared that info (as long as it wasn’t pressury or creepy).

    3. Have to just chime in with a different perspective on the “cards” thing. As a (woman) lawyer, I always have business cards with me. If I meet a potential friend or someone I would like to keep in touch with, sometimes I just quickly hand the person a card instead of doing that awkward dance of asking them if I can give them my phone number and then staring at them while they type it in their phone (and then deciding whether to correct them on my often-misspelled name). I do it because it feels like I’m putting way less pressure on the other person — it’s a quicker exchange, if they want they can toss the card out instead of having to later scroll back through their phone to delete the number they just programmed in out of politeness, if they didn’t remember my name they don’t have to awkwardly ask for it again, and that way they have my email address too if they’d rather use that than call. I certainly don’t use this strategy to show off or look cool. I say this because, while I’m sure there are some people out there that think their business card makes them look cool, I sensed a bias coming from your post – and as someone who largely is in social circles where everyone has cards, to us it’s largely just normal to use them. I hope that if I ran into you somewhere and handed you my card because you seemed like a cool potential new friend, you wouldn’t dismiss me because you think card-wielding people are douchey.

      1. Lo these many months ago, I (a lady) had a crush on the cute receptionist at the doctor’s office but didn’t want to ask him out at work, because that seemed like sort of a dick move. Then, one day, he mentioned he would be leaving for another job soon. Now or never, I thought. Before I left, I scribbled down my email address + some kind of “could we meet up” question, got his attention, handed him the note, and very gracefully made a run for it. He got in touch and we went on a bunch of dates! We are now on opposite sides of the Atlantic and no longer dating, but it was still really nice and I’m glad I took the risk. Cards can work!

    4. Find a good friend to reject you, say “hey would you like to go see a movie this weekend?” and have them say “No. Uh. Maybe. I’ll have to think about it” while you say “oh, ok, let me know what you decide” and then change the subject.

      I’ve totally read that fanfiction.

    5. “Can I give you my number?” is a brief intro question that can lessen the importance of the delivery method.

      A bartender (who probably had a card) once asked me this and it was lovely to be acknowledged as a person who may or may not want his number! I said no, but I still think of him fondly and I bet he gets plenty of yeses.

    6. In artsy circles and some nerdy/fan circles, having an appealing card with personal contact info is cool 🙂 Just depends on your subculture!

    7. In the SCA there are a *lot* of people who have an “social business card” that has their SCA name and contact info and possibly a note about what they do– spinning, fencing, whatever. Same for science fiction conventions. I don’t know about outside those circles, but it doesn’t strike me as at all strange there.

  6. Another few things to keep in mind re: “unclear” answers:

    1) Women are trained pretty much from birth to always be NICE!!! Especially to men. A direct “No” would not be “Nice” so many women default to something less blunt because of literal decades of cultural conditioning.

    2) A lot of men react very very badly to a direct “no.” And the women you’re interested in? Have zero of way of knowing whether or not you’re the kind of guy who will become violent, stalk them, put something in their drinks, harass them at work, rape them, etc. For our basic personal safety, we have to be very careful to not trigger the scary rapey violent kind of men. It’s not about thinking you, LW, specifically seem like the kind of guy who would murder her, it’s about not being able to afford the risk. So, vague answers and subtle escape is what you get, unless and until you’re proven safe. Prove yourself safe by respecting boundaries, for all the women you interact with (not JUST the ones who spark your interest! We notice when guys treat our friends like shit!)

    3) She might not be interested in dating men, or anyone at all, but also not want to come out as non-straight to you and/or the setting you’re in. Plus like, it’s not your business and doesn’t become your business just because you have pantsfeels for her.

    These points are covered by Captain’s point about treating anything that’s not an explicit Yes as a No, but LW might want to consider this more deeply. (This is not an invitation for debate into the “but wrrryyy when I’m/he’s JUST ASKING ONE LITTLE DATE geez”s of life.)

      1. *Squee* ❤

        I figured that, with a guy who writes to a woman for advice, on an explicitly feminist website, odds are good that a more detailed feminist perspective couldn't hurt.

    1. I came here to say a version of # 1 and #2 as well. When you ask a woman out, she is not only reacting to you, LW, asking out her, but she is doing a flash calculation of how likely it is that this interaction you have sprung on her is to become hostile or aggressive, and how to reduce that likeliness while still being “polite” . That’s not really about you, in particular, it is just the way things are when you are female and live in a world where over and over again, your boundaries have not been respected. One way for you to help out in this scenario is do do you absolute best of showing you are NOT going to be aggressive or hostile regardless of her answer. Make that part of your “asking” routine, not just part of the rejection routine that you turn on only after she’s said some version of no. Showing respect for her boundaries, her personal space, her personal life, will get you far regardless if the answer is yes or no.

      1. I’ve seen this phenomenon described as “Schroedinger’s Rapist” — a Dating Uncertainty Principle.

    2. Point 4: assume that women who MIGHT CONCEIVABLY POSSIBLY IN THE RIGHT WIND *mean* yes but aren’t clear about it are Not Right For You. You can cut down on so much angst and dramz and emotional labour by just making a positive unilateral decision that you are going to look for women who belong in the category “able to positively and clearly communicate yes”. Seriously. So very little to regret in that choice.

      1. Yup. From a queer POV: sometimes I will approach women in a way that’s flirtatious-yet-friendly. Often, this results in an interaction that is, on her part, just friendly. Now, is it possible I’m interacting with another queer woman who doesn’t realize I’m flirting, or is unsure and doesn’t want to read into it? Maybe – but it’s just as likely that she isn’t queer, or is but not interested in me. And if she is an uncertain queer lady, that’s fine (been there myself!) but that in turn is going to cause me a lot of stress and probably isn’t worth it.

        1. also a queer lady, and yes!

          There were times in the past when I took the slightly toppier role and I’ve been told by the people involved that it was fine, but actually, it wasn’t fine for *me*. It left me feeling horribly unsure and was just generally less sexy than being with someone who was confidently pursuing me back. 100x better to let someone who *might* be a “well maybe” get away than risk persuading a “probably not” into a “well, ok, go on then.”

  7. Congratulations on using your words, LW! Seriously, good for you! As someone who identifies and was raised/socialized as female, the social norms around dating are one of the areas where I do not entirely envy the role that has been given to those who have been socialized as male. No matter how shy/anxious/inexperienced you are, the dominant societal expectation is still that the man will make the first move and perform all the correct gestures. That is scary! And can feel very vulnerable. Thus, the panic response (“Did I do it right? Did I do it right?! Did I dance the lovely dance?!“).

    It may help to reframe your thinking slightly from here on. As opposed to thinking of this as Your Terrifying Slide Into The Creepy Pit Of Doom, and you are desperately clawing the walls to climb to freedom, think of it as just refining your technique. Using your words and seeking consent are good bases to build on! You have a good foundation! The strategies the good Captain has given you should take you the rest of the way. You got this!

  8. As a lady, I don’t like being pressured for my number in public either, but the first time a guy gave me HIS number, I was surprisingly disappointed: I was pretty young and unsure of myself and didn’t want to do the emotional labor of asking him out. I eventually figured out I could just text guys with ‘It was nice to meet you! This is my number if you want to get together’. When approached, I started asking for guys numbers so I could do this instead of giving my own. Pushers got blacklisted. If I was the approacher I would just give my own number out. .TLDR: when giving your number state it’s so she can ‘text me back with your number if you want to’ – I’d avoid a situation where youre casting her in the role of coming up with a date idea.

  9. Yeah, I don’t think enough can be said for the value of responding to an “I don’t know” with an “Okay, let me know if you’re ever interested” and then just moving on like it’s not a thing. Cause most people aren’t going to mind that you asked if you don’t make it super awkward afterward, and if someone DOES become interested later, they’ll know the offer exists. It’s a great response to cultivate.

  10. Speaking as someone who used to take rejection hard (I didn’t exactly pester but I was very Visibly Sad at people), I think another thought you need to practice is that this is not a judgement on you as a person, not a test you’ve failed. I really wanted to get that ‘yes’ because it meant I was likeable and maybe even kissable, and at the time that meant EVERYTHING to me.

    If some ladies do not want to date you, you’re still a good worthwhile person. You don’t need the yes. Sure you want it, but sometimes you also want a burger and it turns out the burger place is shut – you don’t bang on the door yelling IS ANYONE THEEEERE or try to break in, you accept it and try again another day. There will be other opportunities to date someone. This one lady isn’t a source of self esteem and she’s not your last chance for love, she’s just a lady who you don’t even know that well yet. You don’t need anything from her specifically. Her no is not a huge deal. If it represents a huge deal to you, that’s a sign you’re pinning more on that one lady than she could ever actually deliver.

    1. Yes! Attraction is a funny thing. I have a really good friend, who’s nice, smart, funny, stable (financially and emotionally), and handsome. On paper, he’s the Perfect Guy for me and—I’m sure—a lot of other people (not least his long-time girlfriend, who is also lovely). And yet, I’ve never had any romantic feelings for him and, as far I as know, he’s never had them for me; we just don’t click in that particular way. But that doesn’t mean he isn’t all of those wonderful things or that I am not also a worthwhile person. It means that we each have someone awesome to hang out with and to introduce our partners to. You’re absolutely right that the the LW should practice not seeing every rejection of a date as a rejection of everything about him.

  11. ” However, when you are trying to connect with someone, don’t monitor their feeds and mention everything they’ve ever done back to them, don’t become the person that “likes” every single thing they say (Really you “like” when I wished my Mom a happy birthday 2 months ago?), DON’T click “like” on all their old pictures. It’s about as subtle as skywriting, and it just feels, as you said, creepy to know someone is monitoring you to that extent.”

    Thank you so much for saying this! I’ve definitely had to deal with dudes who hover on Facebook, and it’s uncomfortable, but I never know if I have any right to feel uncomfortable because it’s Facebook, and people can “like” whatever they want, that’s what the button is for. But I’ve had some guys like just about everything, even liking stuff I posted weeks or months ago, and sometimes they like things they can’t possibly understand, like stuff related to my hobby I really could limit to just my hobby group but I’m afraid I’d miss someone. I’ve moved some of these guys to the “restricted” list so they only see public stuff, but if I indicate that I’m interested in an event, that’s public, and they like it. UGH, WHY WON’T THEY STOP? I’m so tempted to pull the plug and just unfriend them but I can’t seem to.

    Some of these guys might just be really active on social media because they’re bored, and I know it’s not nice to assume creepy intent, but I do suspect some of these guys are trying to suck up in the hopes that if I ever become single, I’ll pick him as my next potential boyfriend because I see his name everywhere and we clearly have a lot in common. When actually, regardless of the intent, acknowledging literally everything I post just makes me wanna nope away from someone. Far away.

    I also want to second the point that if someone does like you, they will proactively find a way to spend time with you. If they can’t make it this Friday, they’ll propose another time, or hit you up in the near future and ask you to do something. Women these days are proactive, especially when they know, or at least suspect, their interest in someone is mutual. Very few women these days spend their free time sitting on their beds, wearing gauzy nightgowns, gazing dreamily at the telephone set, waiting for eligible suitors to call, humming the tunes of old, romantic jazz standards to pass the time.

    1. For me, the Rando Who Like All Your Posts and Pics is not even as creepy as the Guy you flirted with or went out with once but weren’t feeling it and then Assumes Every Post Is Exclusively For Him. You post a random meme about drinking wine? He DMs or texts you four minutes after you publish it asking when you guys can go out for a glass of wine. You post an article and he sends his response to the article over DM instead of just replying to your post.

      1. Oh god, this one time I was having a bout of insomnia and going through my carefully cultivated list of People On Twitter Who Don’t Raise My Blood Pressure (a private list, since nobody needs that kind of Am I Off Or On This List pressure) and retweeting interesting things while trying to get back to sleep, and this dude IMs me because clearly Signs Of Life On Twitter mean that I am awake and ready to chat, right? and when I say “Hey I’m in the middle of my sleep cycle” he says something snippy about tweeting in my sleep.

        He would later send me a FEELINGSBOMB around midnight on a day when I had an early morning meeting. (I told him that I was not prepared to deal with that email, and fortunately that was the last conversation we had.)

      2. Oh man, yes, this guy!! I had one that I’d talked with as a friend over one messaging platform (we shared an online hobby), I realized he was flirting, so I pulled back because I didn’t feel that way about him…and he proceeded to message me on three other platforms. And then he became This Guy on Facebook, liking and commenting on my every post. The last straw was really when I got my hair dyed and unlike everyone else commenting on the pic, he DMed me about it. Dude! Go away!!

      3. This kind of intense scrutiny is why I had to put my mum on restricted Facebook access. She’d message me about any event I RSVPed to, or ask for an explanation of a post instead of just assuming you know, that it wasn’t for her. She treated my online life like it was a performance for her consumption, rather than a place where sometimes I just wanted to connect with friends without feeling constantly monitored and suffocated.

    2. Oh man I have had this happen. Somehow he went through DOZENS of photos, liking things from MONTHS ago, but managed to ignore everything else including that I was married. And then asked me out. Nooooooooooo dude.

      1. Aargh! Yeah, been there, too and it is absolutly terrible, especially when they ignore you being married. I was once sitting on my ex-husband’s lap when I was asked for a date.

    3. Allison, you do have a right to feel uncomfortable. Some reasons you have that right are:

      1. You have the right to feel whatever the eff you ACTUALLY FEEL. Which, right now, is uncomfortable.

      2. You’re uncomfortable because their behavior doesn’t have a normal, ‘non-uncomfortable-making’ explanation. It’s not the fact that they’re liking a post you made. It’s that they’re liking EVERY post without regard to actual consideration of the post’s content, its relevance to them, or their impact on you. They aren’t engaging with you as a human being.

      3. You’re uncomfortable because they haven’t been so egregiously creepy that you can obviously point and say That Was Creepy without them being able to say things like But All I Did Was and I Didn’t Mean Anything By It and Gosh Why Are You Reading Into Everything and Did You Think I Like You Or Something Because I Don’t.

      4. You don’t have to make a binary choice between wide open borders and complete shut out of everyone. You don’t owe them access to you until they cross a line that THEY agree with. They’ve already crossed a line. You are allowed to be uncomfortable. You have a good reason in this case – but you don’t have to have a good reason or any reason at all! You sure don’t have to have a defensible thesis as to why you’re uncomfortable. They don’t have to agree that their actions would make you uncomfortable. You are allowed to decide based on your own feelings and nothing else!

      It took me forever to learn this. They don’t have to agree that they’ve crossed a line! You don’t have to be scared of their response. You can block them on FB and if they ask why they can’t see you, you can be like yeah weird huh? I dunno. Facebook’s been acting up on me lately.

    4. YES! Sometimes I interact with someone after a long hiatus and about 30 min later they “like” a picture of mine from years ago. It always gives me a weird queasy feeling. Usually I’m also all dressed up and not pictured with any dudes oddly enough.

      I love the last paragraph. I mean I don’t know about you but I have some great gauzy nightgowns and I have the “dreamy stare” down pat.

  12. This is all great, advice-wise, but I think the Captain may have missed an opportunity to have the LW consider these scenarios from a woman’s point of view. Many women won’t give a hard “no” to a man because they are afraid for their safety and/or socialized to worry more about “letting the man down easy” than having their desires be heard. Once you consider this, you begin to see every, “I’m not sure” for what it really is – buying the woman time and space to get away from you to where she can safely say “no”. Pushing someone in this position to have to directly say the “no” right away violates so much more than boundaries.

    1. Daphne, I’m not sure where you’re coming from here. The Captain said that the guy should interpret any vague/non-“yes” answer as a “no.” She didn’t suggest that women should be more assertive about saying “no.”

  13. Hey there, Don’t Wanna Be a Creep! I applaud you for working on your self awareness and boundaries. You’re doing the right stuff to examine your responses to brush-offs and awkward situations. If you keep on like this it will make you very dateable! I want to address something in your letter that really jumped out at me: “I was glad to get the straight-up answer, *but I had to push her boundaries to get it.*” No, my friend. No. You did not *have* to push her boundaries to get a clear no. She gave you vague/brush-offy answers which you actually *correctly* read as her not being that interested. Pushing her boundaries was a choice you made. Hoping to what..change her mind? By doing that, you are forcing someone to say NO more than once or more forcefully than they would have otherwise. You are backing them into a corner. It’s not cool. Take the Captain’s excellent advice around taking anything other than YES!!! as a NO. You actually already understand this but you are pushing past it even when you know you shouldn’t. Quit doing that and you will level up significantly just by doing this one thing.

    1. Great point, well made.

      I think this LW might be stuck on there being a specific script that needs to be followed—as in, guy asks girl out, girl gives a straight yes or no answer. When someone deviates from this script, he wants to get it back on track by forcing that straight yes or no. I’ve encountered this kind of herding in conversations in every aspect of my life (work, family, and romantic partners—I apparently don’t stick to other people’s scripts very well) and it’s super frustrating to be talking to someone and feel like nothing you say matters because the other person is waiting to hear some magic word or key phrase before you’re allowed to talk about something else. At least the LW’s script ostensibly allows for more than one acceptable answer to his question.

      I would advise him not just to stop doing this when he asks someone out, but also to examine if he does it with other people in his life and, if yes, to stop doing it to them, as well. Like you say, he should just accept that unless the answer is specifically yes, then it’s no and move on. If the answer is a “soft no”, like the ones he’s been getting, then it’s especially important to “hear” the woman’s answer and allow her to change the subject or gracefully exit the conversation, rather than corralling her into one of the pre-scripted conversational endpoints.

  14. I do like the idea of making more specific invitations rather than open ended I like you, can I kiss you, etc. That’s an awful lot of pressure to put on someone who doesn’t know you very well.

  15. LW, I think you’re going places! It’s very awesome that you recognize your behavior in the past has been not cool and you want to change it. Don’t be too hard on yourself – we have all been there and done things in our dating past that make us cringe or think, “Holy wow did I misread that situation.” You are not alone. The most important point for you I think is to treat anything less than “Yes, I’d love to” as a no and move on accordingly. And please, never again, ask “But why?” when a woman says no or seems non-committal. I get asked “But why?” by my children hundreds of times a day and I think if I heard that question from a man who was trying to date me I would erupt with rage. (That could just be my specific circumstance, though.)

    1. It’s not just you. “But why?” comes across as arm-twisting, which would make me see red.

      1. True. I had a guy friend recently tell me that my standard answer of “No, thank you, I’m not interested” was not kind, and I should lie and say I was into someone. Boy, did I rip into him about that one!

    2. Last summer, my roommate and I had two solicitors in fairly short succession at our door. We kindly turned them down. They both “But why”ed us. It drove me nuts. I instantly went from feeling a little bad at turning them down to wanting them gone asap. There are precious few scenarios in which good things come of a But Why. Just let people’s no (or noncommittal waffling) be a no. There is no explanation that will be satisfying to hear.

  16. As a Cranky Married Old (I am approx. 9 million years old in cat years), I don’t get hit on … ever, anymore, BUT I think

    “Treat anything that is not “Yes!!!!!” like “No.””

    is excellent advice pretty much everywhere.

    For example, I get that there are a lot of people who feel wriggly about asking for help at work. But if I *ask* you whether I can help, and your answer is “well, um, I think I’ve got it” – pal, we are adults in a professional environment. I am going to do you the courtesy of taking you at your word, and we don’t work at a psychic readers’ hotline. I’m happy to help you out when you’re swamped, but I’m NOT happy to magically intuit whether you are being coy.

  17. LW, I can’t tell if this is a pattern, but you mention specifically in the kiss example that you waited until the two of you were alone, and it sounds like you might also have been alone with her in the second conversation you mention. Those are the sort of responses I give where I am not thinking AT ALL about whether I am attracted to the guy, I am thinking “how can I placate himself long enough to get myself out of this situation?”

    It probably feels safer for you to ask in a situation where you won’t have any witnesses to your embarrassment if she turns you down. But for her, it’s a situation where she won’t have any witnesses if you respond to a “no” with violence. (Or if you decide that “yes, you can kiss me” means “I am now entitled to have sex with you.”)

    You don’t have to wait for a crowd or interrupt an ongoing group conversation – that can be its own unsafe situation in another way – but think about making that kind of first approach in a situation where she knows she has backup and a quick a way out if necessary – with other people in the room at a party, a semi-public space like a coffeeshop, over email or text, etc. You know she doesn’t need to worry about that with you, but she doesn’t, not yet. You’re more likely to get a straight answer (yes *or* no) if you pick a situation where she feels safe giving you one.

    (And if you don’t know how to get in a safe-ish situation where you still feel like you can ask, something “Hey, let’s get coffee at that place downtown tomorrow” is a good way to start and, like the Captain said, much easier to say no to.)

    And remind yourself that it’s okay if other people see the interaction because it really, truly is No Big Deal. Remembering that it’s Not A Big Deal and asking in a situation where people will notice if you make it a Big Deal might make it easier in the moment to moderate your responses, too.

    1. (Or if you decide that “yes, you can kiss me” means “I am now entitled to have sex with you.”)
      This is a really excellent point, too – sometimes women are noncommittal or indirect because they’re not just thinking about the question you’ve just asked them, they’re also trying to suss out the subtext. Like, sure, I’d love to go somewhere private with you and talk, but are you really asking me for that or for something else?
      Unfortunately, there isn’t much of a way to reassure women on this point. Someone who says, “Can I kiss you?” when they mean “Can I put my dick in you?” is just as capable of saying, “Really, just a kiss” and not meaning it either. All you can really do in that case is accept her no.

  18. Hello LW! Cheers to you for asking for direction and I think you are on the right path, and the Captain’s advice is spot on.

    I’ll add to the, ‘but why?’ question. Everyone wants to know that – those of us who have insecurities, are socially awkward, have self-esteem issues – however there is no satisfying answer to be gained in the asking, especially if you are asking someone who does not know you very very well.

    Look at it this way. You meet Interesting Person, maybe visit a few times in social situations. You enjoy talking to IP, IP enjoys you too. (and as an aside, don’t ‘Flirt’. I don’t even know what that word means. I’ve been told, You blew it, that dude was totally flirting with you!, along with/on the other hand, You sure were flirting with that dude! And I’m all, I thought we were just talking? Was there A Thing happening I didn’t pick up on? Whatever. Just be yourself.)

    So you enjoy IP and you say Hey this is Good Times, do you want to get together for X event next Y date? And if they say No (in whatever flavor way they do) remember this is not a reflection on who you are as a person. Maybe they are: divorcing, involved, pining for someone else; out of a bad relationship; out of a wonderful relationship; recently fired, recently hired; about to move to somewhere. You look like their sibling/parent. You are too [tall/short/thin/fat/young/old/blonde/brunette/an intergalactic alien* pick-your-whatever]. Point is, none of those things have anything to do with who you are in the essential sense. You just didn’t click, and it does take two.

    Take their no with grace. If you really did have a connection, be pleased you possibly made a friend and make the most of that.

    *Unless you are an intergalactic alien, which if so, I don’t know what to tell you. My unsolicited advice only goes so far.

  19. I can’t emphasize enough how important it is to ask someone a clear, actual question – and to ask it in a way that doesn’t put them uncomfortably on the spot.

    When you ask someone, “Can I kiss you?” their “No” answer feels very much like a rejection of you. That’s a really uncomfortable thing to do. Considering that you yourself have struggled with shyness in the past, I hope you can see how deeply awkward and difficult that type of rejection can be for other people to give.

    When you ask someone, “Would you like to go on a date?” their “No” answer is a rejection of the date, not of you. It’s much easier to give.

    When you just blurt out how much you like someone, you’re not even asking a question at all – so I don’t think it’s a surprise when you don’t get an answer.

    Finally, I ask that you remember how difficult social interaction can be, and to give these women some of the compassion and understanding that you would like for yourself. I’m not saying that you’re not doing it right now! I just really want to articulate this – I often see men who struggle with asking a woman out condemn women for not giving a clear yes or no answer. “It was so hard for me to get the courage up and she couldn’t even give me a clear answer!” I see just a tiny hint of that lurking in your post – as though if women would just give you a clear answer, you wouldn’t be acting in creepy ways. (For the record, I want to clearly say “acting in creepy ways” and NOT “you are a creep” because I don’t think the latter is true.)

    If social interaction is hard for you, it’s probably hard for a lot of women, too. Yes, in a perfect world the soft rejection would not exist and women would have the confidence and assertiveness to Just Say No. But in a perfect world, you wouldn’t have depression or social anxiety. We don’t live in that world. If you want understanding for being socially awkward yourself, I respectfully ask that you extend that same understanding to women who have trouble Just Saying No.

    1. This is an excellent point.
      Treating women as People includes recognizing that some women are awkward people.

      1. Insert comment about importance of recognizing awkward ladies on a website run by a lady whose title is LITERALLY Captain Awkward.

  20. My rule of thumb is “make exactly one pass, NO MORE.” I’ve kicked myself over being too shy to approach people a few times, so one is better than zero. But I figure that after saying something once, said person has been notified of my interest and they can take it from there – whether it’s an immediate “heck yeah”, or a “wait what”, or a “thanks but no”. If their opinion changes, they can let me know. I figure that people won’t forget – and if they do, that’s an excellent indicator of indifference.

  21. It might help to adjust your expectations. I would be shocked if anyone just said, “No thank you, I would prefer not to kiss/date/get to know you better.” It just isn’t done, for a variety of reasons that other commentators have detailed. It sounds like you have a script prepared “yes” or “no” answers, and then panic when you get neither. You’re suddenly forced to improvise and the conversation goes off the rails. Very rarely will you get a hard no – possibly never. So you should prepare yourself for “Yes!” or “silent response combined with deer-frozen-in-headlights facial expression,” “I think I need to freshen my drink,” or “Huh, I’m not sure,” or “Umm, yeah, so uh, well then” or even, “Yes, sounds great, I think I need to go talk to Sally right now, okay bye.” (That last one is somebody that couldn’t think of a polite no, said yes instead, panicked, and then fled the scene.) I think role-playing is an excellent idea, so that you don’t have think on your feet in the moment. Ideally you’ll find yourself saying the right script before you even know what’s happening. If you can move the conversation back to neutral ground, it is enormously relieving for anyone you’re talking to. Maybe not right away, but if you can circle back around to them the same night, it lets them know you’re not going to be awkward and they don’t need to avoid you. (It’s also very attractive and will make that person feel much safer around you. For anyone on the fence, this will definitely work in your favor.)

    1. I’ve done it, I’ve given honest answers, because I’d rather be a little rude up and possibly presumptuous front, than have some guy I barely know following me around, hovering over me on social media, hoping either I’ll change my mind and give him a chance, catch feelings, or they’ll have “an opening” (usually a time when I’m newly single and vulnerable, and likely to welcome any male attention even if it’s disguised as a shoulder to cry on). I’ve said “I don’t feel that way about you,” I’ve said “I’m not interested in ‘getting to know each other,'” using quotes to emphasize that I know the “I just wanna get to know you better” game, I knew the intended result, and I wasn’t interested in that.

      And I’ve done this because I too have been the idiot who clung to someone on social media after a soft “no,” thinking that okay, they don’t wanna date me right now, but if I just show them how great I am and don’t let them forget me, eventually they’ll be intrigued and wanna date me. Now I know not to do that, but I also know when someone is doing it, or when they might do it.

    2. LW, I agree with Thistledown that your difficulty comes from not knowing what to do when a conversation goes off script.

      Trying to script a conversation is setting yourself up for trouble because the other person never seems to know their lines. You can script your first line and have a plan of action that depends on their response (continue/disengage), but using a script even for your second comment is perilous. I suppose you could script your disengage line, but you better have practiced it so that it carries no hint of scripting, or you’ll set off warning bells.

      A conversation is not a chess game: the players’ next lines are not limited by rules so you cannot plan your strategy out X number of ‘if they say this, I’ll say that.’
      Role play improvising, as opposed to rehearsing scripts, so you can respond naturally and comfortably. You can have phrases that you’re likely to use, but being comfortable is what will make them work.

      Best of luck and high props for recognizing that you’re not making the impression you want to make and working to improve it.

  22. Not directly related to the situation here, but worth giving a shout-out to: The Stop, Drop and Roll Technique!!

    I have been struggling with a request regarding things (I really don’t want to, or need to, do) as a member of a non-profit board ; and the SD&R technique is an excellent strategy.

    Thanks to the LW and to the Captain, for helping me learn something new!

  23. Lots of great advice here already, LW. I don’t see a lot of response to the part about you saying “I like you”, though. And I see that in two different ways.

    First, there’s the starting-by-flirting thing, where you can inch into getting to know each other better without declaring explicitly that you are (a) interested and (b) available. Someone proposes coffee. Someone else responds enthusiastically or doesn’t. If the two people enjoy each other’s company in the low-stakes meetup, they might both work into conversation whether they are available for romantic entanglement or whether it’s more complicated (moving to Vancouver next month for grad school, a single-parent with shared custody) or not available (monogamously married, doesn’t date your gender, etc). Then there might be another get-together without any declaration of intent, and neither of you says “I’m attracted to you” in so many words yet. For many people, that set of customs allows people to become closer friends without feeling embarrassed about one being attracted and the other not interested.

    However, there’s also what my friends call the “geek-flirt”. In this kind of direct approach, you don’t leave room for plausible deniability, but say directly “I like you. If you are interested, I would be interested in [going on a date, going on a series of dates and maybe becoming primary partners, having sex occasionally, whatever] But if you’re not, that’s totally cool. I hope I haven’t messed our friendship up by asking because I like spending time with you and the rest of the crowd. You don’t have to give me an answer now, just let me know sometime if you’d like to talk about this.” In my experience and observation, this does not work well with people who don’t already know each other well from spending time together in groups of friends. It sometimes works well (meaning, either the two of you agree to pursue something or you establish quickly that it’s not going to happen and you get to keep being friends) for people who are in more complex situations like about-to-move-to-Vancouver, committed to raising children, people who are polyamorous, etc.

    I totally agree with the Captain’s recommendation that you ask once and don’t pursue a maybe, That works for whether you’re trying the first approach or the second one. Just, when you’re deciding whether to say “I like you” as part of your first invitation, be aware that many women will be uncomfortable about that, since in their experience it’s too fast and too direct and might be a clue that you won’t take no for an answer. Only do a geek-flirt approach if you think you’ve built up enough credibility over months and maybe years of association and friends-in-common that she is likely to believe that you will take no for an answer. And if you’re not doing the geek-flirt thing, don’t say that you like her or are attracted to her before you’ve established that she enjoys spending time with you.

    1. Yea I am so uncomfortable with people saying they “like” me if we haven’t spent any time alone together. If some acts that way it may lead me to steer clear.

  24. When you suggest handing a card, does this mean your business card with your work email/phone?

    1. Literally a piece of paper with your name and a way to contact you.

      People are really overthinking the card thing, huh?

      1. You noticed that too, huh?

        I feel like when I have mentioned the “GIVE YOUR contact info don’t DEMAND someone else’s” guideline in similar conversations, people’s responses often are trying to object to not being “allowed” to demand a stranger’s phone number without sounding like the kind of pushy jerk who demands strangers’ phone numbers.

        1. Unless your number is engraved upon parchment and delivered by an owl, she will not call!

          Or, like, she may not call anyway, don’t sweat it.

          1. I have experienced a distinct lack of owls in my corresponding life. Gotta work on that…

          2. …to be fair, if the number was engraved upon parchment and delivered by an owl, I’d definitely call. If only so I could ask about their time at Hogwarts.

      2. The concept of going out with a pre-printed written down move in your pocket definitely appeals to the nerd in me. But it also reminds me of my own teen love note disasters. Unfairly so since one is chill and the other was definitely overkill. It’s actually in the same bracket as ‘here’s a napkin with my number on’ and ‘Karen has my number if you’re interested’.

    2. I have a business-etc. card with my name, a brief description of the kind of work I do, email, and phone number. I got it for freelance work, but have also used it for “text/email me if you want those political links we were discussing.” (This is handy if you don’t always have pen and paper in reach.)

  25. Also, man, we’ve all been there. Maybe not this exact situation, but the “why would I say that? what’s wrong with me? Oh look! I’m still talking, why can’t I stop?” moments. The earth never opens up and swallows you whole when you wish it would. But, embarrassment is an excellent way to say I’m sorry. It’s basically how you demonstrate that broke the social order accidentally because you’re awkward and not purposefully because you’re a creep. If you ever run into any of these women again, I’d feel free to turn red and apologize. (This can actually be quite charming – so long as you keep the focus on them. “I’m so sorry I made you feel uncomfortable.” and not “I’m such a creepy looser and no one will ever love me.” That second is just making them uncomfortable again.) If this is a close friend group, maybe confide in a female friend. Tell them how embarrassed you are and that you’re working on handling rejection better. It’s going to help you if you can change the narrative from “LW is a creep who kept demanding to know why Sally wouldn’t kiss him” to “LW’s really working hard on his social skills; he’s mortified that he made Sally so uncomfortable.” Everyone has an embarrassing story like this, so they’ll likely relate to you. Mortification and groveling apologies are underrated are excellent social skills to develop. (Again, so long as they’re not “I should just kill myself” traps that attempt to manipulate the person you’ve wronged into feeling sorry for you and comforting you. Don’t do that.)

    1. Confiding in a female friend as you’ve suggested may be helpful, since LW’s motive is wanting to fix the behavior. If he was the Nice Guy (TM), that strategy could backfire. I had a “dodged a bullet” situation once in college – a friend relayed to me that her boyfriend’s friend wanted to ask me out. I found this particular guy very unattractive in both looks and attitude, and told her I wasn’t interested in him. She said I should “give him a chance” and tried to push, but I was Really. Not. Interested. Next time he came up in conversation she was telling me that he’d said I should “get my head out of my ass”. Wow, who wouldn’t want to go out with such a charmer who obviously thought so highly of me?

      That one and this one guy who asked me to dance once, I politely said “no, thank you,” and he threw a temper tantrum. “NO?!? What do you mean NO?!?” Definite bullet dodged.

    2. Please don’t confide in a female friend. Why make your emotional issues yet another slice of emotional labor on some woman’s plate.

      1. I think that falls under the kind of emotional labor I’d be happy to do for a friend, if by friend we mean “someone who will also do emotional labor for me and who I like hanging out with,” not “someone who leeches off me for free emotional labor and occasionally thinks I should give him oral sex because he’s been so nice.”

      2. I said a female friend, because I don’t trust my guy-friends who say things like, “I know he walked all over your boundaries, but he’s a great guy. I mean, that one ex has a restraining order against him, but everyone deserves a second chance! They never proved his third wife was murdered.” (Maybe the men you know are better at risk-assessment.)

        This apology should absolutely not be an “I’m so creepy and sad, please comfort me and teach me how to make women like me,” sort of apology. More of an “I’m am so sorry I was so weird towards Ann at your party. I’m trying to put myself out there more. Apparently I still need practice as I had a melt down and chased her around your house saying, “why don’t you want to get to know me?” I promise I’m working on handling rejection better, but if Ann seems leary of hanging out with me again, she has some good reasons.”

      3. …because friends often confide in one another and want to help each other? Turning a female friend into an unpaid therapist is a shitty thing to do, but that’s not what it sounded like Thistledown was suggesting.

  26. If you get an unclear answer from a women (like “I don’t know” or “I’m kind of busy this week”), I think the best approach is to be straightforward. “I won’t ask again, but if you decide you’re a yes, then you know where to find me.”

    When I was single and dating, I was always super impressed who were able to roll with rejection in this way. It demonstrates a lot of confidence.

  27. Although I like the idea of asking someone if you can kiss them, you are asking it way too early. That’s a question for much further along the process*, like after a first date has gone well. If you are asking someone if you can kiss them at a party where you have just met, she is going to panic and quit the scene. If you have travelled as a group, as in your example, unfortunately you’ve just put her in a pretty uncomfortable position.

    * I’m not implying that dating is a process as such, but I couldn’t think of a better word to use here.

    1. Yeah, I’m interested in meeting new partners, I’m flirty and enjoy hanging out and getting to know people, I love kissing and sexy stuff…

      …and I would be SKEEVED if anyone but a close friend who had already established mutual attraction just straight-up asked to kiss me.

      (After an awesome date, in which it was clear that this was a date activity we were doing together? Yes, then you may ask. But I’d feel cornered and uncomfortable if someone just brought it up at a party.)

      I love the idea of giving YOUR contact info (personally, cards are fine by me, but if nobody has paper/pen, you may ask to put it in the MEMO SECTION of my phone — don’t try to stick yourself in my contacts, but asking if you can type your number/e-mail is okay in my book.)

      I do like people who can take “no” or “not now” or “maybe” for an answer — I’ve ended up dating a few people who I initially said no to, who RESPECTED MY RESPONSE AND STAYED COOL, and who I liked better once I got to know them as friends.

      Don’t hold out for hope of that, it’s not going to happen often — but women do notice people who behave well and are respectful of boundaries.

      Good luck, OP — you’re asking the right questions, and I hope the advice to your post proves helpful 🙂

    2. I had an exception to this. It was a New Year’s party and early in the evening the guy asked me if I was there alone, and if, so, did I want to be each other’s Midnight Kiss? BUT 1) it was done very low key, 2) there was no expectation of a yes, 3) he gave me a few moments to think about it, and 4) the agreement was totally that it’d only be one kiss unless we were both into it and only if we didn’t get any better deals.

      Turns out he was a FANTASTIC kisser and we spent the rest of the party talking and kissing. But I think this is the exception that proves the rule.

    3. I felt that way too. If someone who I had met just a few times in a group setting just asked me if they could kiss me, I’d probably feel a little panicked and deer-in-the-headlights myself, even if we had flirted a few times before. At that stage in the game, I honestly don’t know for sure if I’m interested in that way yet. I’d want to at least go on a casual date first. I realize people sometimes don’t do things in that order, but yeah, that seems a little early to expect an enthusiastic yes to a request for a kiss.

    4. Yes, this. I can’t imagine a situation where I’d want to kiss someone I had just met. Flirting (I think for a majority of women) serves to establish interest in getting to know the person better, that’s it. Just give her your contact info and say you’d love to see her again, that’s plenty. It also feels safe to the woman.

      Good luck and all.

  28. “Mortification and groveling apologies are underrated are excellent social skills to develop.”

    However, they can also be easily overdone. I am a lifelong compulsive apologizer. Don’t do that, either.

    1. This is a really good point that I hadn’t noticed! Too often, apologies become all about the apologizer – as in, “I feel so terrible and I am an awful person, please spend enormous amounts of emotional energy in reassuring me and listening to me put myself down.”

      I kind of think an apology should never be groveling – it should be honest, and without justification, but when you reach the point of groveling, it doesn’t make anyone feel better. It just raises the amount of investment the “hurt” party needs to put in to ending the interaction.

    2. This is an excellent point! If you’re five minutes late to lunch, nobody wants to listen ten minutes of your self-flagellation! If you’ve just fallen face-first into somebody else’s crotch, now is the time to turn purple and start stammering. If you had an accident in somebody else’s car, you should start talking fast (and promising to pay for repairs and to give them rides to the airport for the rest of their life). Apologies where you make somebody who should be mad at you comfort you, are not apologies so much as shady emotional manipulation. But I do suspect that most folks reading Captain Awkward fall into the over-apologizing camp rather that the under-apologizing camp.

  29. A friend once gave me an odd book called “The Cowgirl’s Guide to Love.” (By odd I mean things like: it frequently refers to men as “John Waynes.”) But among some questionably personality typing was also some good words to live by, including, “Test the Brakes.” The book has a whole section on making sure your John Wayne knows how to take ‘No’ for an answer. I think it’s sound advice.

  30. Once upon a time when I was in my early twenties, I ended up in a position where two people I knew were both attracted to me. Now, my super supportive grandfather (who’d been my closest family member) had just died and I’d just fled from a pretty emotionally abusive family situation, living in my own apartment for the very first time. I was in the process of figuring out who I was, so my answer to both of these people was: No, I’m sorry, I need a friend more than anything right now.

    Suitor #1 took this answer and:

    Sent me long handwritten feelings bomb letters. Bought me expensive gifts I wasn’t comfortable with. Made a show of being my friend for, like, a week, before getting angry I wasn’t immediately falling into bed with them. They convinced all my friends at the time into trying to set us up (one of these people tried to get me drunk at a party to ‘make it happen’! whoo). When this didn’t work, they proceeded to sulk, pout, express jealousy over my friendships with other people, write guilt trippy stuff on social media when I did anything fun without them, eventually growing angrier and angrier until they decided to tell all our mutual friends I was an abusive psychopath through a series of very carefully targeted social media posts, they had me ostracized at my workplace (I’d helped them find employment there), and gaslighted me into fleeing that social group (and job!) entirely– all within six months of my grandfather’s death.

    Needless to say, I never went out with them.

    Suitor #2 took this answer and:

    Said that was totally cool. Spent the rest of that visit to my city hanging out with me, playing video games, and going to museums without bringing the issue up again. They never pressed for my time. When a few months later they invited me on a trip to a nearby sci-fi convention, it was expressly with a group of friends, expressly platonic, and expressly as a “hey, you seem like you need a break, want to join us?” They never brought up their earlier question. They never tried to question or negotiate my no. They were more than happy to just hang out with me and spend time with me. They respected my grief and my recovery. When I mentioned in a sad blog post I wished I’d get a letter telling me everything would be all right, I received a postcard a few days later that said exactly that, with little cookies drawn on it. They didn’t sign it but I knew who it was from. They were so kind and such a good friend, I ended up seeking them out when I ran into them in social groups. And, finally, after some time and a lot of personal recovery, we were vibing really well together and they asked me out again in a very low stakes situation I….

    Totally panicked and said no. They backed off IMMEDIATELY, and I repeat, never pressed the issue. The rest of that convention proceeded as normal with no weirdness.

    And then two weeks later when I pulled my head out of my ass I e-mailed them going: SORRY I CHOKED I ACTUALLY I MEAN YES DO YOU STILL WANT GIVE THIS A TRY

    And anyway, we’re married now.

    Now I want to stress that I’m not trying to suggest persistence or performative friendship was the thing here that made me realize I did like Suitor #2 and wanted to smooch them. Suitor #2 was far less pushy and performative in how they expressed their attraction to me. What really made me realize I wanted to smooch Suitor #2 was their respect for my boundaries, their awareness of my current situation, and the fact they never treated my friendship like it was a shoddy conciliation prize. This was a person who was just deeply interested in who I was as a person, romantic or platonic, and through that I felt comfortable getting to know them better. Through that I was able to realize how much I valued and yes, loved their company.

    I guess what I’m saying is, relationships should be born of a mutual respect and a genuine affection for the other person. Someone who can gracefully take a ‘no’ and still show interest is someone’s wellbeing separate of that romantic interest will have many happy relationships with people, be they friendships or otherwise.

    1. oh geez, I’m sorry. I didn’t mean to write an essay. Please delete this if possible! It is maybe a bit too besides the point.

      1. This is very much what I was trying to say (elsewhere) but you illustrated it much better.

      2. This was great! I have had the #1 friend. It wasn’t fun. So happy that you had the # 2 friend as well and that it worked out for both of you in the long run.

    2. This is such a wonderful story! 😀 Great example too of the difference between a Nice Guy(tm) and a nice person

    3. I *love* the phrase “my friendship is not a shoddy conciliation prize”–if you don’t want a friendship with me, why would I want a friendship (or more!) with you?

      It positively encapsulates why I detest the “friend zone” mindset.

    4. I love this story except for the crappy suitor 1’s alienation tactics. But the end makes up for it!

        1. also it was a postcard with a picture of various planets because she said she wanted a “message from the universe saying things would be okay”. It was not cookies. But I guess my crayon planets are sort of cookie-like. I am not the artist of our pair.

    5. I related to this story too! It reminds me a little of me, and how a guy showing interest in me ever would have me run awkwardly panicking. In eighth grade, a long, long time ago, a guy I’d been friendly with (maybe even flirted with, but I don’t know because I’m still so awkward), asked me to dance…at a dance…and I fled and kind of stopped talking to him. To his credit, he did not act any differently, and I still think about what a cool dude he was and how I wish I’d been more mature and less awkward so we could at least continued to be friends. I hope that is encouraging to the LW in some way.

  31. LW, all I have to add to this excellent advice is that you should educate yourself about emotional labor, and here’s why:

    There’s a cognitive dissonance in your letter which you yourself point out. In the moment, you say that your question was “left hanging,” but later, you recognize that in fact it was not: you received a soft no. To me, this demonstrates that you know that you’ve been rejected, and what you’re actually seeking is some form of emotional closure. You’re also putting it on this woman to do the emotional labor of giving you that closure, which is not okay.

    Men are taught their whole lives that women are responsible for handling their feelings. It’s not your fault that you’ve received this message. Now that you know you’re doing it, however, it is your responsibility to stop doing it. Work on this by googling, reading, and talking with your *dude* friends about this. (Don’t make it women’s job to educate you — that too is emotional labor.)

    I’m a very anxious person and have a lot of sympathy for the feeling of needing resolution or closure when something has made me anxious. It’s okay to feel that way, so long as you don’t make your feelings the problem of the person you just asked out.

    1. Talking with his guy friends may not be all that helpful – odds are they need some reeducation on this point too.

      1. So they can all go take Feminism 101 together.
        I think the point about not demanding that women educate them is important and worth making.

    2. This! This! This!

      I once rejected a guy who I had gone out on a coffee date with, and shortly afterward I received this long message to the tune of, “Hey Zombie Bunny, thanks for being so polite about this, and since you were so polite, could you maybe also tell me what I did wrong? Because [long breakdown of all his other encounters with females, and their rejections, and his palpable confusion], and I really want to reverse this pattern. Please give me feedback if you can! I understand if you don’t reply, but [long guilt-inducing reason for why he wouldn’t actually understand].”

      And you know? I actually almost fell for it. I fell into the role of Female Emotional Labourer and started drafting a reply along the lines of “Well, sometimes people just aren’t compatible, you’re not a bad guy, but maybe don’t lunge to try and kiss someone you’ve never met before instead of saying hello?”. And then I stopped. And a little voice in my head said, “Hey, let’s say he changed those particularly bad behaviours. Would you change your mind and want to see him again? Nope. None of that will change the fact that you didn’t click. This dude has whole scores of people, from friends and family to therapists and religious leaders, who can all point him in a better direction. It doesn’t have to be you.

      I know it’s tempting to get your answers straight from ‘the source’, but don’t make it the job of the person who said ‘no’ to help you find someone who will say ‘yes’.

    1. Ack! I mentioned this upthread, without reading to the bottom where you have a link to the piece. You are awesome!

  32. Dear LW,

    I’d like to address “but why?”

    I believe you’re asking this question in hopes you’ll hear a cheat code.

    No, really.

    I think you’re hoping to hear that the woman you asked out would’ve said yes if you’d done it differently.

    She wouldn’t have. She said no (however gently) because she doesn’t want whatever you asked. That’s the “why”.

    Maybe if you were a different person, or maybe if she weren’t married, or gay, or maybe if- oh who knows? It’s all contrafactual, and out of your control.

    She said no.

    I’m pleased you’re a person who asks, and I’m sure if you follow the Captain’s advice, you’ll find women who do want to date you.

    Good luck.

  33. I haven’t read all the comments yet (I’m about half way down right now), but it seems to me as if neither the Captain nor most of the comments until that point actually answer the question:

    “How do I remember to bow out gracefully in such a moment?”

    The LW _knows_ what is creepy, and _knows_ that soft no’s are no’s, and that he should not push after that. I don’t think he actually needs all that lecturing on consent. The question is specifically about how to become able to put that knowledge into practice in the very moment. It isn’t about what he thinks about how he should act in those situations, but how he can actually stop himself for long enough to remember. How to stop the automatism he feels trapped in.

    I mean, the only ones touching on it that I have seen are the ones suggesting practicing rejection situations by role playing with a friend, but maybe we can come up with more? (I personally have no idea.)

    1. I think simple works best in that kind of situation. LW likes a woman. He knows that he wants to ask her out and that he’s bad at what comes after the no. What if he doesn’t ask and puts it on her? “Hey! You’re cool. Here’s my number. I’d love to hang out sometime. Call me if you’re interested.” and then that’s it. As a woman, I can safely say that the odds of her saying no in that moment are slim. We’re programmed to be nice. She’s going to say “ok, cool, thanks” take the number and shove it in her pocket. Don’t ask again. Don’t bring it up. Don’t mention it. Keep chatting or move on to something else, but leave it on her. If she’s interested she’s going to call. If she’s not interested she’s not going to call but LW has avoided the word vomit that comes after the rejection.

    2. I agree with you. As an impulsive, in-the-moment, not really self-aware or mindful person, the gap between KNOWING what to do (after the fact, or well before) and actually DOING it in the moment is enormous. I get caught up in a swirl of emotions and wants and needs and distractions and, oh, fudge, I did it again didn’t I.

      Some ways I’m trying to bridge the gap:
      -After-the-fact analysis (instead of shame spiraling): What went wrong? What would the right response have been? Can I picture myself having done that? Why not? What was I feeling/thinking when it happened? What can I do in the future to make myself more likely to choose right?
      -Preplanning (putting my anxiety and overactive imagination to work for me): What am I about to do? Will something about this situation cause an event? Could it? Why? How can I avoid that?
      -Visualizing making the right decision either in a situation I flubbed, or in a future situation that may or may not happen (the point is visualizing behaving differently; it worked for roller derby, maybe it’ll work for bad habits)
      -Journaling all of the above

      Thing I haven’t tried for reasons (shame, that reason is shame):
      -Role playing with a trusted friend. I actually really like this idea, LW, as your problem is pretty narrowly focused. You could start with non-romantic interactions (“Can I have some of your chips?” “Uhhhhhhh…..” “Ok! I’m going to refresh my drink/walk my dog/subject change!”) and work your way up to more emotionally charged situations. Maybe this person could even nudge you if they see you having trouble in every day situations…? YMMV.
      -Mindfulness techniques

      LW, if you run into motivation issues (change is HARD; I’m still pissed that my instincts all seem to be wrong and some days I really don’t want to do better), reread the Captain’s response and all these comments. They’re good reasons and should be good motivation. I really think you can do this. I believe in you!

    3. That’s a good point! I think my advice would be to have some graceful scripts prepared for a soft “no”. A phrase that’s come up a lot in people’s suggestions is “Okay, let me know if you change your mind,” followed by either a change of subject or a mild disengage.

      Perhaps the LW could have the phrase “okay, let me know if you change your mind” already prepared in their head before they ask the question. That way, in the moment, they can avoid getting into a panic spiral of “oh god I’ve just been told no and now this is awkward how do I change this situation?” They know how to deal with the situation, and so it becomes less of a big deal.

    4. I don’t even think LW needs to necessarily practice with a friend; I think that it might be helpful, on an emotional preparation level, to assume the answer is ‘no’ unless it’s a clear and IMMEDIATE ‘yes’. Anything other than that is a ‘no’. So what do you do if you don’t hear a ‘yes’? ‘No worries, just thought I’d ask’, and CHANGE THE SUBJECT. Or if (like me) you’d be too awkward/embarrassed in the face of rejection to change the subject, excuse yourself from the conversation.

      Also, all of the other things: make sure that you’re not putting the woman in an uncomfortable situation where she may feel like she can’t safely say ‘no’. Accept that you will probably never get a direct ‘no’, and let go of that expectation. Ask for low-stakes interactions–coffee sometime, instead of a kiss right now.

      That’s what I can think of at the moment.

  34. Really great, until the end. I’m a woman, and I’m Conservative. I don’t like Trump, but I prefer him to the alternative. WHY does wanting to be with someone include the idea that most women are Progressive and so you must be too in order to be lovable?

    HALF of people (including women) are Conservative, and guess what? We’re lovable too. Don’t change to be something you’re not.

    1. Cool and I will not stop advising young men to work for women’s rights if they want to love women. Don’t pretend to be someone you aren’t – be better!

      If you are an American conservative who doesn’t agree with Trump you have arguably MORE work to do right now.

    2. Hi, Tammy, you’re wrong.

      Most of the world isn’t American. Even if your claim is true about the USA (already questionable), it is not true about the rest of the world. Most of the planet defines “conservative” well to the left of American republicans, as well.

    3. That bothered me, too, for all that Americans of all political persuasions who don’t like Trump have a lot of work do to right now! I felt like it risked tying romantic success to political engagement. I don’t want to risk anyone thinking of my sexuality as an acceptable political bargaining chip.

      With that said, even if it doesn’t affect romantic success, it’s still an important thing to do.

      1. I don’t think political action earns female attention but if you are a dude asking “how do I date ladies” I am gonna throw this out there every time and I mean every time: What are you doing to make the world better for women, including ones you don’t want to sleep with?

        Not “do this and we’ll sleep with you” more like “come correct or don’t come at all.”

        Every time.

      2. My aunt’s sister, a Trump supporter, also supports LGBT rights (as in genuinely happy for me and my wife when we got married.) When the actions and the views clash, believe the actions. You may be surprised – even pleasantly so.

        1. Jenny, what the fuck.

          I guess it’s great that your aunt’s sister isn’t a literal piece of shit to y’all’s face, but Trump’s chosen vice president thinks its okay for parents to send children to forced “conversion therapy.” Trump just ran up a trial balloon for purging transgender people from the armed forces that’s designed to create maximum fear and hassle for them as well as test out the rest of our tolerance for that kind of bigotry. When someone with the power to make policy makes policy, believe the policy.
          Or, to make it personal, when I lose my health insurance in one of these dumbass repeals I’ll remind myself that your aunt’s sister is really cool though? I’ll tell my students all about her when they & their families get deported. She has a good heart! She celebrated at your wedding!

          Lots of “nice” people voted for Trump and lots of “nice” people are super okay with white supremacy and xenophobia and anti-Semitism and misogyny and we’ll all be grappling with it for a very long time.

          Y’all, I’m tired. This is my website. I am not a newspaper or an ad supported publication and I don’t have to pretend to be neutral or to weigh both sides. Official CaptainAwkward.com policy is that Donald Trump is a piece of shit and if you voted for him or “prefer him to the alternative” I deeply, deeply, deeply question what kind of person you are. It’s not “just politics” or a morally neutral thing. We have a secret ballot in this country so if you feel comfortable telling people about what you did then I feel comfortable judging it. If that makes you uncomfortable, cool? I am so uncomfortable with all of this. I mostly don’t talk about it here because if I start I won’t stop, but it’s not like how I feel is a hidden surprise.

          Comments are closed.

    4. Hi Tammy,

      Has it occurred to you that you’re not lovable?

      Just checking. Because someone who opposes other people’s rights, freedoms and very lives is fundamentally unloveable.

      Hope that clears that up.

    5. Tammy, the conservative platform is basically racism and homophobia wth a side of “screw the poor and disabled.” That’s not remotely lovable. If you feel bad about having that pointed out, perhaps you should do something about it.

    6. “The alternative” would be who? Someone who doesn’t court white supremacists? Someone who doesn’t brag about committing sexual assault? Someone who is not very likely a traitor? There’s such a long way to go between Trump and even someone like Jeff Sessions (who also courts white supremacists, but more subtlety) that I find the sentiment that Trump is a better alternative than literally anyone so bizarre from a reader of this blog.

      Women’s rights being human rights is only political if you think the patriarchal hegemony is the correct way in the first place.

  35. LW, in addition to all the other advice you’re getting, I think it’s worth asking yourself: where is the panic coming from? The examples you’ve given are not women you’re never going to see again. All will not be lost if you don’t seal the deal right this second, assuming you ever had a chance in the first place. So if you don’t get a definitive answer, why is that a problem requiring an immediate solution? Is it going to stop you from asking other women out in the interim? (It shouldn’t.) Are you worried it’s going to make your future interactions with them weird? (That’s not something you’re really going to know until the next time you see them, so why not just see how it goes and address any problems if they arise, instead of trying to get out ahead of a problem that may not exist?) Are you not going to be able to think about other things without clear feedback? (That’s something you can work on without their participation.) Is it something else? Answer that, and I think you’ll have a much better handle on how to corral the brain weasels.

    1. CA has linked to this in the past and I think it bears repeating here:


      Especially if you’re ‘late’ getting into the dating scene (Hi!) putting yourself out there and hearing that rejection can feel like exactly that.

      It takes some time to absorb that rejection doesn’t mean you failed the dating game – you’re getting the opportunity to exercise a skill that’s *part* of the dating game.

      There’s a saying among horse folk that you’re not a real rider until you’ve fallen off at least three times. Eventually you just stop counting.

      Heck, if you want, mentally frame approaching someone as ‘politely accepting rejection practice’. Then the worst that can happen is you’ll be pleasantly surprised!

      1. Heck, if you want, mentally frame approaching someone as ‘politely accepting rejection practice’. Then the worst that can happen is you’ll be pleasantly surprised!

        I think this is very good advice, actually!

  36. Great answer, Captain! LW, asking is hard, uncertainty is hard, and receiving a no (or soft no) is hard. I’m really glad you are asking and aware of how you need to respect the answers.

    I know how difficult ambiguity is to deal with. And some of it may be that someone wasn’t thinking about dating and doesn’t know on the spot how to respond. Like others say, treat a maybe like a no, and she will certainly not forget if she later decides she’s interested in meeting you for a date.

    There’s also extra complexity–and thus potential uncertainty–involved in a situation with friend groups or activity partners. Even if you have spent time in each other’s company, you might not know key things about each other, like sexual orientation, relationship status, or what that person’s like to talk with one-on-one. This might go against the grain of much of the advice here, but this might be a case for an ambiguous ask: “I’d like to get to know you better. Would you like to get coffee next weekend?” Obviously, only do this if you are happy to be platonic friends, though this has strong overtones of a date. In this case, treat a maybe as a no. If the person suggests bringing other people along, go for it, but that is probably also an indicator that they would not be interested in a romantic date, unless they suggest it with the words “double date.”

    If they ask for clarification (“Is this a date?”) TELL THE TRUTH: “If you’d like it to be. I was thinking about asking you out, and I realized we only know each other in the context of (all our friends/activity). I don’t even know if I’m your type, but I do know I like hanging out with you when we (group activity).”

    Ugh, maybe this script is too indirect. Thoughts from others? It may be helpful in cases where one or both people usually share very little about themselves. (E.g. If you’ve been told you are “quiet” or you often hang back.)

    Alternately, a great way to avoid uncertainty is to stick to situations–like online dating–where the other person is prepared to be asked out.

    Good luck!

  37. Seconding/thirding/nth-ing the advice that it might make things easier on both you and your crushes to make date requests pretty specific, if you aren’t already–as in, suggest an activity, a time when it would take place, and make clear you’re asking as a date (wanna be my date to this comedy show Thursday? Would you want to go out for dinner friday, like, as a date?’ etc).

    That way, if you get a yes you can jump straight to planning the details, if you get a soft no, you can take it gracefully as a no, and if the person you’re asking out is genuinely interested but can’t/would rather not do the particular thing you’ve suggested, they can parry with a different plan (‘I’d love to but I work Thursday, how’s about the county fair on Sunday?’)

    I am almost 35 and feel like a total teenage dork saying ‘do you want to go to the new cheese curd emporium, like, AS A DATE’, but I swear that little bit of up front dorkiness saves you both an entire cheese factory tour worth of ‘is this a date?? how do I know??? what if they think it’s not and I think it is and…’-level awkwardness.

    1. I am married but tell me more about these cheese curds…could we visit them as friends?

    2. ALSO please consider making your date offers both public and inexpensive. I had another lady recently suggest hiking in the woods as a first date, and we are not going on a date after all because my brain went “this sounds like the beginning of a criminal mind episode, and I will be the rotting corpse, and someone will lament the internet and catfishing and poor life choices.” As for expense, if it’s $$$$ and you don’t split the cost, it creates a certain pressure for like, idk, sex right away. Plus that is a lot of theoretical money to blow on someone before you’ve even been on one date.

      1. Public, inexpensive, and of short duration. Committing to one beer or coffee lets you cheerfully duck out after 20 minutes if you’re not feeling it. Committing to a three course meal only prolongs the agony.

      2. Yes, the one time I went to the house of a guy I didn’t know very well (a bunch of his friend were all hanging out there – I was new in town and very lonely), they ended up telling “hilarious” stories about torturing animals to death. And that one time they all committed a hate crime. Never again.

  38. LW…I once knew a guy who acted like you. The night I met him he told me that he wanted a girlfriend and was not at all convinced when I told him that I wasn’t interested. He asked me out. I said no. He asked me why. I felt uncomfortable. This went on and on for months as his friend was dating my friend and our paths frequently crossed.

    The difference between you, LW, and the guy I knew? You are aware that you are doing something that is making others uncomfortable and want to stop. He never did. He briefly had a girlfriend but the last I heard he was still single and making women uncomfortable. He has reached out over and over on social media to the old friend group asking all the women out and then asking for set ups. No matter how many times he’s been told he doesn’t believe that he’s the problem. LW…it sounds like you are so much more self aware than he ever will be. That’s a huge thing.

    I think CA and the commenters have offered some amazing advice here. Do you have a female friend who might be willing to help you role play scenarios where you might get turned down or even moments when you may have to turn a woman down? It sounds like you have a good handle on who you don’t want to be, but now it’s time to work on who you do want to be and it sounds like that is more of a matter of being more confident in your own skin in those moments.

  39. Specifically about phone numbers:

    When someone you (generic you) don’t know well has your phone number, that entails a certain amount of risk. If they turn out to be a weirdo, they might use it to stalk you, or hack you, or send you dick pics, or sign you up for cat facts, or write it on the bathroom wall (or on the internet) where other weirdos could also find it and use it for these things.

    When someone you (generic you) don’t know well asks you for your phone number, there’s a certain amount of risk in that interaction. If you say no, they could get angry or violent or stalky. If you say yes and you aren’t 100% into them, they could accuse you of leading them on, which could also make them angry or violent or stalky. You don’t know what’s going to happen, and there’s a risk to every decision.

    So if you (LW personally) ask someone for their contact information, you’re asking them to bear both of these risks.

    Whereas if you (LW personally) offer them your contact information, you’re offering to bear the first risk yourself, and eliminating the second risk.

    This can only reflect well on you in a potential dating situation. You’re recognizing and bearing the consequences of your actions, and you’re acknowledging the reality that the women you’re trying to date inhabit – both of which are things that creeps rarely do.

  40. Dear LW,

    I have known many people in the same situation in which you are in – and I find it awesome that you want to improve your behaviour. In my opinion a person who is willing to admit that there is a fault in their own behaviour or thinking is a very brave one, for encountering one’s own weaknesses takes enormous amounts of strength and courage.

    I am myself a woman and have all my life been mostly asexual (there have only been a couple of people I have been sexually interested in) so I have been in the receiving end of these situations. I do love many people, but mostly not in a sexual way but emotionally. That has lead to quite a few unpleasant situations.

    I find it in a way very brave that you have directly asked people for a date instead of awkwardly hovering about but not being brave enough to ask for a date – although asking for a kiss sounds to me somewhat disturbing. Maybe this is a cultural thing, but if I had been there, asking for a kiss would have crossed my boundaries in a bad way. The only time I have accepted a kiss from a person I had newly met was when I met my spouse. I was the one who asked him out and I had known his siblings for decades before that so I felt like I could trust him.

    I was left wondering how well did you know these women? Did you make sure whether they are single (or in a relationship in which there is a mutual agreement that finding new companions is ok) or interested in males – or sex at all? I wish there was some kind of socially acceptable way to ask these questions. In the years I have been following this awesome blog so many of my own questions have been answered by The Captain that now I am wondering whether The Captain knows any cool and casual ways to find out about this things.

    I understand the urgency of finding a romantic partner, I have witnessed it so many times and tried to console my friends and give them hope. Still, there is nothing wrong with friendship – but I do not mean friendship as a poor substitute for romance! I mean friendship, for its own sake. I would advice for trying to be patient, for getting to know people better first. Most of my friends who were in the situation you are now in have found spouses among the circle of their friends after getting to know them well first so that they could trust each other and the awkwardness was much less awkward.

    I am left wondering why do you feel the need for romance now? I do not know how much time has passed between these instances of asking people out, but if all of these have happened within a year or so and in the same group of friends it may not help. What is driving you? Is it loneliness or is somebody pressing you to find a girlfriend (like a family member, perhaps a parent?)? People enjoy being loved for the sake of themselves, not filling the spot of a desperately needed general romantic interest. Is there anything you could do to be more satisfied with your own life and yourself?

    Have you tried to find a date with any other method? Just like The Captain I, too, found my spouse via OKCupid. It was swift from there: both of us knew we were looking for a potential partner and that we were interested in the same things and we shared the same values. There are people just like you out there: perhaps a bit shy, a bit unexperienced – and I am sure they would be glad to meet you.

    Take care of yourself – and kudos to you for your bravery in asking advice!

  41. Hello, LW! I recognize your impulses to follow up in my own (that I have learned to quash down). I’m a poly queer lady who mostly likes to date other queer ladies/enbies, but OMG is it hard not to accidentally make people uncomfortable until you recognize the pattern.

    Sometimes I will send a perfectly crafted text and then realize I am staring at my phone, waiting for a response. My brain weasels kick into gear like “whyyyy haven’t they responded to my perfect text? Was it not perfect?” And I want to FIX IT but I have learned — often through my own experiences with often cis men — that more messages are the worst.

    The Captain’s advice to do literally anything other than try to fix the gnawing sense of something wrong in my gut is good. Move on with your life! But if you’re like me, your brain has a whole litany of negative thoughts for you now: nobody likes you; you’ll die alone; you used too many/not enough emojis; basically a heaping pile of self hate. My brain weasels say it can be fixed if I just confirm that this other, external person doesn’t hate me.

    But take it from me, relying on other people for validation is both deeply unsatisfying and leaves you pre-groomed for potential abuser! Plus you can’t get validation all the time, so you will ironically never be happy, just forever chasing the high of external approval.

    What helps me not send That Awkward Series of Increasingly Demanding Follow Up Texts is

    1. Not wanting to be That Person from Feminist Tinder (worth a visit for “what not to do”)
    2. Knowing that when people push my boundaries, I get uncomfortable
    3. Thinking of a mental list of reasons for the delay/meh response that is NOT whatever crap my brain weasels are spewing (eg Maybe they are in a movie. Maybe their battery died. Maybe they’re not sure about whether the cafe you invited them to can accommodate food allergies. Maybe they had a migraine and didn’t want to commit to anything until they could think clearly again. Maybe they just need time to make decisions, I do!)
    4. Do literally anything else other than bothering them for an answer. Read/make calls, also consider finding ways to give myself that burst of accomplishment that don’t involve other people so I don’t sabotage eventual relationships with codependency issues (that may not be you, but oh is it me).

    I think in a way I’m at an advantage because, existing as a queer femme, I’ve got constant reminders of what it feels like when people want to walk all over my boundaries. It’s in media, it’s in the news, it’s everywhere. It is an icky feeling, and I don’t want to make anyone else feel that way. But maybe if you consume more media by women, or think of a relatable experience in your life, it can help you remember not to do the thing.

  42. Basic feminism is that Women are Human Beings. If LW relates to women with this principle first and foremost, instead of seeing them as potential conquests, I’m guessing that he’ll be amazed at how well things can be in his life.

  43. Some people can be spontaneous in their interactions. Some people always know just what to say in the moment. That’s not me. I am a Planner and a Scripter. If something I didn’t plan for happens, my script short-circuits and heaven only knows what will come out of my mouth.

    I get the vibe that you might be similar to me in that regard. (If not, I apologize, and feel free to ignore this post!) Maybe when you first starting asking people for dates/kisses/whatever, you had a plan for yes, and you had a plan for no… but you didn’t have a plan for what would happen if the answer wasn’t as straightforward, and so you ended up reacting in ways that were less than ideal. Not great, but understandable. But the good thing is that now you realize that that’s a possibility, so you can plan for it. You can say to yourself, “Maybe instead of saying ‘yes’ or ‘no’, she’ll be vague or non-committal, in which case I’ll take it as a ‘no’ and gracefully back off.” Congratulations, you are now more prepared to react in a non-creepy way in the future!

    (Speaking of this, I’m really glad I read this today, because I’m planning on asking someone out soon myself and I don’t think I had a plan for an answer that wasn’t yes or no! Now that I’ve considered that that’s something that could happen, I’m less likely to be blindsided by it.)

  44. This won’t be everyone’s cup of tea but as a woman who struggles with saying No, I really appreciated attending a Cuddle Party workshop. The title is a bit of a misnomer/bait and switch, it’s mostly a consent workshop where you get lots of practice giving and receiving No in a low stakes environment. You start off asking something like “can I touch your shoulder?” and replying “No, thank you” or “No, but you can shake my hand.” The reply to “No” is “thank you for taking care of yourself.” The idea is to experience a (strange, new) world where women don’t have to brace themselves for a defensive barrage upon saying no. After the workshop is the actual cuddle party, where the same rules apply, and there is no pressure to cuddle anyone. It might be beneficial. http://www.cuddleparty.com/

  45. Oh Sad Emoji Guy. I think I dated his cousin, Sad Panda Guy. (As in, literally texted the actual words ‘sad panda’ to me when I wasn’t responding to him quickly enough. I recoiled so hard I nearly dropped the phone. No.)

    CA put it best: “Don’t renew the request.” You’ve put the ball in her court. You don’t need to walk over to her side, retrieve the ball, and serve it back to her again in case she wasn’t paying attention the first time.

    Reciprocity = YES.

    (I say this as someone who’s been both ‘That Girl Who Won’t Take A Hint’ and ‘You Again? Why Won’t You Take A Hint?’)

    Also: CA’s advice to write down your number is good. RESIST the urge to update said advice for this century by saying ‘Here, program my number into your phone’. Why? Because so many guys will ask you to do this, then say ‘Okay, now call me so I’ve got your number.’ Even if you don’t, she’ll still be tensed for that other shoe to drop.

  46. Something about “But why?” LW, are you attracted to every woman you meet? If you are not attracted, is there a concrete reason? Why is not a question we should ever have to answer. The fact of the matter is, people tend to be attracted to a portion of the population, not all of it. And it is generally not as cut and dried as “he’s a racist’, or “not really into gingers*”. Sometimes it’s just that there isn’t that undefinable spark. Apparently Channing Tatum is attractive, but you would never know it by me. I know nothing to his detriment, but we all have different tastes.

    *disclaimer — really into gingers.

  47. LW, it sounds like you already know that continuing to pressure women to date you after they’ve already given a soft “no” is a problem. And it sounds like you know that it would be better to hear any non-“Yes!!” answer as ‘no’ and move on with your life. The problem is that in the moment, you’re reacting rather than thinking, and your unthinking reaction is the wrong one.

    If that’s accurate, then I think you have two options. Either 1) you find a way to reprogram your reactions, or 2) you find a way to ask people out that doesn’t give you room to go into that unthinking-reaction mode.

    For option 1: This is largely a muscle memory thing. When humans are freaked out and not thinking clearly, we tend to default into the most familiar pattern of behavior, even if it’s not really right for the situation at hand. Try roleplaying asking someone out and getting a soft ‘no’ with a friend, so you can learn to react appropriately over and over again in a safe environment where someone who cares about you can help you catch it early if you start going off track. Work up to asking people out for real once you’re confident that your default behavior is what you want it to be.

    For option 2: Try asking someone out in a less on-the-spot way. Email? Text? Online dating site message? Give them your contact info and let them choose to reach out (or not) at a later time? Regardless–asking someone out face-to-face means they have to respond right away, and it also means that you have to handle their response on the spot. Using a more delayed method means you both get time to think things over and plan your response, instead of reacting in the moment. Having that extra time to process might help you choose less aggressive responses (and it gives you time to ask a friend to read it over, if you’re really concerned about being accidentally creepy).

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