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#231: How do I learn how to say the right thing at the right time to people I’m interested in?

Ahoy, cap’n!

So, I’m a fairly attractive and well-socialized guy with a self-esteem problem that makes it difficult for me to assert even that I’m fairly attractive and well-socialized. For the most part I keep that under control, but romantic situations are challenging.

Being fairly attractive and well-socialized, I don’t have much trouble meeting women. Many of my friends are women. The problem is getting from being friendly to being physical.

I’m not the Mayor, and this isn’t another friend zone complaint. “Friends” is easy and comfortable, and “more” is — or feels — complicated and scary. I don’t know how to get there, I don’t know how other people get there, and much of the time it seems better to stay put.

What am I supposed to say or do? How do I know when to say or do it? How do I avoid panicking or feeling skeevy?

Thanks!

Hi there.

1) What am I supposed to say or do?

To get started:

  • Would you like to go on a date sometime?
  • You are really cool and I love hanging out with you. Also, you are pretty. Can we go out sometime?
  • Can I buy you dinner sometime?
  • There is this cool (thing) happening next weekend. Will you be my date?
  • I feel nervous and awkward asking you this, but I would love to take you on a date sometime.

On a date that’s going well (by which I mean you are having fun and think the other person is having fun and you are having a good conversation about stuff you’re interested in and everyone is keeping up and smiling):

  • I’m having a really good time with you, thanks for coming.
  • You look fantastic. I love that (color on you, thing you’re wearing)

When you feel like you might want to kiss the other person:

  • I would really love to kiss you now. Is that okay?
  • Can I kiss you?
  • Would it be okay if I kissed you?

Leave the magic moment where you know without words to the experts (or Future-You, who has more experience with this). Use your words and ask.

Say the kissing stuff is really good and everyone seems to be enjoying themselves.

  • I love kissing you. Could we go somewhere else and do that some more?

2) How do I know when to say or do it?

You don’t. So try saying it when you feel like saying it, preferably as close as possible to when you feel it, when you’re sure the object of your affection is paying attention to you (e.g. You’re already having a conversation that she seems to enjoy – she’s not giving one word answers, looking at her watch, texting/calling her friends, trying to watch a movie.) May I suggest online dating, to give yourself practice asking people out in a context where some romantic interest is the default?

3) How do I avoid panicking or feeling skeezy?

You don’t. You may well panic and/or feel skeezy!

The moment where you go from not-kissing to kissing is fraught with vulnerability and potential awkwardness, and the space between two people who could-be-touching-maybe-but-aren’t-touching-yet can seem infinite and uncrossable. That’s what makes it so awesome and sexy when you actually connect. Nervousness? Wondering if people feel the same way you do? Wondering if you’ll screw it up or they’ll screw it up? These feelings are inherent to sexual and romantic connection and discovery, even for people with a lot of experience. Experience makes you able to be more confident (and handle rejection better over time), but it doesn’t change the vulnerability you feel with a new person you like.

You’ll get rejected at least once. Probably a lot. If you do the asking out sooner rather than later, before you get too invested, and you accept that rejection and/or lack of connection is the default setting, what’s wrong with rejection?

Let’s do some Rejection Math:

I went on about 10 first dates with people I met on an online dating site in the last 6-7 months, give or take.

I turned down AT LEAST 50 people on the spot – either by not replying to their messages at all, or writing back and saying thanks but no thanks. I initiated contact with another 10 or so who didn’t want to go out with me, or we wrote back and forth a bit but never actually made plans. Let’s put the “never even met up” count at 60 for the sake of easy math. I am picky and busy.

Of the 10 I went out with, I liked two enough to go out a second time.

I became great friends with one of them after a brief crush/flirtation period where I clearly liked him more…er, differently… than he liked me (and said so out loud).

I fell in love with the other one and he with me.

That’s 68 nos, 1 maybe-no, and 1 YES!

Rejection is a normal part of dating.

REJECTION IS A NORMAL PART OF DATING.

I was not harming the dudes I didn’t want to go out with by rejecting them, and the dudes who didn’t want to go out with me were not harming me.

If you pre-reject yourself by panicking, overthinking, and avoiding, you will never get to the good parts of life and love.

If you’re looking for some rubric where I tell you signs to look for to help shield yourself from rejection, I don’t have one. Women are people, people are diverse in what they want. All you can do is ask for what you want and be gracious and patient until you get it. If something seems to be going well, watch for reciprocity. People who like you will act like they like you. They will help you out with awkward moments and be proactive about communicating and making plans.

4) What’s the difference between a would-be writer and a published author?

The published author finished a book, sent it out, got rejected, took some feedback, revised the book, sent it out again, and kept doing that until the right person pulled it out of the giant pile of other manuscripts at exactly the right time. It took a combination of persistence, optimism, dumb luck, and the subjective tastes/wishes of the person who read the book and liked it.

P.S. That last thing was a metaphor.

P.P.S. Seriously, that’s all I’ve got. It IS that simple. Every single person who is romantically/sexually involved with another person got there because someone was brave enough to cross that tiny-yet-infinite-space and say the awkward thing out loud.

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42 comments
  1. Graf Orlok said:

    All really great advice, captain. Amazing how simple things are when we can realize we’re not perfect, bound to make mistakes, and ask for what we want!

    I can second the online dating recommendation. I was a little nervous about it, and still don’t vouch for its efficacy, but it is nice practice and fun to meet lots of random people you wouldn’t otherwise.

  2. This is a great post. One which I’m sure you will refer to often. I love the ‘no bull’ approach and the notes on rejection. Without getting all ‘Eco psych’ I think it is human instinct to shield ourselves from rejection and the nasty feelings that come with it. But it is a gamble. You roll the dice, use your words, and see what comes up. Sometimes you’ll get a yes, others a no. It’s when that ‘yes’ turns into the warm fuzzies that you’ll realise all those rejections were totally worth it. Good luck LW!

  3. Awesome post, and surprisingly relevant to my life. Dear LW, I am kind of in the same position, and let me tell you – it feels like I am the Most Awkwardest Penguin in the world! I’m doing everything “wrong” and I have zero experience to draw on and also am not really familiar with the social scripts this person may be using to interpret my behavior, so I cannot guess how I am being received…I feel like I am using a slang dictionary from the 1950s, in short, without being sure if I am talking to someone who is familiar with them. And yet? This can’t be that special of a level of awkward, I don’t think. And sometimes Using My Words makes things feel less awkward to me, and sometimes it feels more awkward, and none of this seems to relate AT ALL to whether or not the other person is perceiving me as awkward, because zie does not seem to be considering me awkward at all until I say “well that was awkward?” and zie goes “oh, I am sorry, I was tired” and I go “oh. Well, that explains that then…” and auuugh.

    So even if you think you are the Most Awkwardest Penguin, you aren’t. I am officially the Most Awkwardest Penguin (even though I am really not), so you can relax, because there is someone in the Awkwardeers awkwarding it up more awkwardly than you.

    (ok, bedtime for me, obvious…)

    • I feel like I am using a slang dictionary from the 1950s

      I am taking that metaphor.

  4. Elysia said:

    LW, these two sentences caught my attention: The problem is getting from being friendly to being physical. and “Friends” is easy and comfortable, and “more” is — or feels — complicated and scary.

    Do those two ideas link, in your head? Because if they do, that might be something worth examining. I used to buy into the cultural narrative that It Is Best To Be Friends First. I liked it because I have poor self-esteem, and I thought that being friends meant I could establish trust with them and romance wouldn’t be so scary. For me, this hasn’t really been true. (Your mileage may vary.) It helped me a lot to realize that it’s okay to look for an emotional and intellectual and otherwise non-physical spark before being looking for a physical spark – there’s no rush, even if physicality is something you want. I wanted to kiss someone on a first date, but I wasn’t ready, so I didn’t. Later, he asked if he could kiss me, and I was not scared, and we kissed, and it was great. Point is: I had to dig to figure out why I felt stymied.

    Also, my gut and groin are saying something important when physical feels too complicated and scary: it’s not right for me. (time/place/person) Might that be true for you? It might not be! I totally get it if you feel like it’s scary simply because you’re not sure what to do or how to do it or whether the other person is on the same page! Been there! I sometimes find sexytimes scary even as I am enjoying answering my desire for sexytimes. Using my words and trying again has helped me feel less consistently scared, or less unable to act in the face of my uncertainty. (The Captain, she is a wise person.)

    Also, for what it’s worth, I bet a whole lot of people feel like they don’t know how they get to “more” – they just stumble along and sometimes it works and sometimes it doesn’t. I don’t think you and I are missing out on some big secret of the world if we’re not sure how to make physical happen. :-)

    • The problem here is using friendship to “get” sex. Most people legitimately want different things from different relationships. Establishing one kind of relationship and then putting the expectation that it will turn into something else gets you off on the wrong foot. It’s not impossible, but not really a good system. This isn’t “friendzone”, a term used by sexists to shame women for believing they have a right to control who they have sex with, but just a reality.

      If you’re going to spark with someone, after all, they’re probably feeling it early, too. If you like someone and you don’t make your move and they don’t, it’s probably because they don’t feel it. So when you make your move months later, they have every right to believe you’ve been crushing on them for months and conducting the friendship on false premises.

      • Elysia said:

        Establishing one kind of relationship and then putting the expectation that it will turn into something else gets you off on the wrong foot.

        Totally agree! I did not mean to say/imply otherwise, and if I did, oops! My apologies for saying something problematic. (And no more commenting before 8am for me.)

      • Greg said:

        They have a right to suspect that, certainly. But that isn’t necessarily what happened. I’ve been in situations where I’ve known someone for months or even years, and I was “maybe/not sure/I don’t know” on the romance question, but “yes” on the friends question, and I only made my move when knowing them for a long time pushed me off the fence. Other times people change in a way that a “no” to romance early in the friendship changed into a “yes” later on.

      • Jeff said:

        Perhaps this is unusual, but I often don’t feel the “spark” until I have known someone for a long time. I have a couple friends who I asked out more than a year after I met them. They said no, but we are still good friends. I am very glad they did not assume I was crushing on them the whole time, or that I was only their friend in hopes of getting sex.

        • human said:

          Me too. I think the timing of “sparks” works differently for different people and it’s unfair to assume everybody is the same.

        • wondering said:

          I’m the same way.

      • Vicki said:

        I’m another who sometimes takes a while (months to years) to develop a spark, or to become aware of it. Not always: my girlfriend and I were striking sparks off each other within about 12 hours after we met. But often.

        Given that I can take a long time to develop/recognize a romantic or sexual interest in someone, I know that there’s a significant chance, by that point, that the other person doesn’t feel the same way, and maybe even that they’ll think I was crushing on them for a long time. But the answer is still to use my words, and accept that the answer might be “no, thank you.” Yes, there is a risk of awkwardness there, but I think there’s always some risk in expressing that sort of interest.

        That said, and relevant to LW’s question, gender may be a factor: I’m female. A woman developing an interest in someone (either gender) over time is probably less likely to be perceived as having done friendly things while secretly crushing on the person, or waiting for them to notice her.

  5. Sofi said:

    This is the best.

  6. monsterzero said:

    Hey LW, I’d say that if you don’t get rejected MORE than once, you’re doing it wrong.

    I did it wrong for many, many years. I was terrified of being rejected and so never took any chances at all, ever. And so I was really lonely for years, or, a couple of times, in a bad relationship. Bad because I waited for them to pick me; I wasn’t actually choosing the people who were right for me.

    Finally I started taking chances. I got rejected, and each time it got easier. It was NEVER anywhere near as painful as I had feared. Also, consider dating more than one person at a time. The stakes with person A are way lower if you’ve got a date with B tomorrow and with C next week.

    “I would really like to kiss you,” used before the end of the third date, worked very well.

    • rosi5 said:

      Monsterzero, thank you!! I’m in a similar situation to LW, and am holding back on using my words/making a play due to low self-confidence and fear of rejection. It can be so hard to remember that rejection is totally normal and that it doesn’t confirm every insecurity one has about themselves.

      • starskita said:

        Not in terms of relationships, but rejection and self-confidence are in all walks of life when interacting with others.
        What I’m trying to say, is that no matter how badly you screw it up, there will be another chance and you’ll learn from the mistakes. Maybe with another person. Maybe in another place. But unless you’re screwing up asking out the daughter of a mob boss (don’t try that for your first one) there will another chance.

        Speaking as one who as an adult still has hour-long crying spells in public, hyperventilates when nice people come help me, and has lost a multitude of friends by being the “bad roommate” before I figured out what I was doing wrong.
        I’ve made new friends, and I try to minimize the amount of bizarre behavior, and sometimes things work out.

  7. theLaplaceDemon said:

    I want to second (third?) the recommendation for online dating. You 1) Get to meet new people! 2) It’s already got “date” as a default setting, which feels less complicated, 3) Related to #2, it’s easy to ask someone out before the stakes are high – since the expectation of everyone on the site is Date, it’s normal to ask them out after one or two messages are exchanged, and finally 4) It helps you gain confidence and get used to the practice of dating, making it way less OHMYGODSCARY and way more “awesome, I get to spend an evening (and maybe more) with a potentially really cool person!”

  8. BlackHumor said:

    Thanks for this! I kinda have the same problem as the LW: it’s very easy for me to START a conversation with a woman I like, but actually asking her for her number or on a date or even giving her MY number is really hard.

    It’s better than back in high school when I couldn’t even start the conversation, because at least now I have a lot of female friends (Here I should probably reassure you that I’m not being the guy in that XKCD strip; most of my female friends I am no longer seriously interested in asking out.) Unfortunately, still no dates.

    So, LW, all i have to tell you is, YOU ARE NOT ALONE.

  9. xenu01 said:

    I can see the draw re: being friends first, and I know it has worked for some people, but personally, that never worked for me. I feel like “friends of friends” (without having them actively set you up) can be better, because you have common interests (your friend! The fun activities you engage in with that friend!) and maybe have a chance to get to know them in a low-pressure way but also there’s not that whole “will I ruin the friendship” problem.

    Of course, I would advise you meeting a FOF and feeling all sparky to use your words soon, so as to avoid the pining-after situation. Generally, I find that I know right away when I am interested in someone. It’s not interest or sexy feelings that grows slowly, over time, it’s trust, love, and understanding.

  10. LW said:

    Thank you for the response, cap’n. I’m sure you’re right, but the idea of saying something — even as boring as as “I’d like to kiss you” — makes my insides hurt. Time to get some practice, I guess.

    To the commenters who asserted that I’m becoming friends with women only in the hopes of getting sex, I’ll skip what I’d really like to say in favor of a polite suggestion that they’re leaping from flimsy evidence to a hurtful conclusion.

    • DBegh said:

      Oh, LW, I can feel you. I haven’t done much all that asking people out thingie either. If I hadn’t read dating advice from strangers on the internet (thanks to the captain and all commenters btw), all I’d have to guide me through this messy world would be the mainstream media. (This would be SO TERRIBLE. I can’t even fathom the consequences.) But yeah, I haven’t really taken that advice to the real world yet. (Unless you count a drunken flirty talk that didn’t last long.) I’m pretty ok with that for now, as finals are coming soon and I’m waaay busy right now.
      To conclude, you’re afraid of asking people, and I’m too! That’s because we’re not used to it. I mean, I used to be terrified of going to the barbershop! Now I’m not, I know how to use my words to ask for a proper haircut. My point is not to compare people you date with hairdressers. What I mean is that I trust my ability to eventually handle common interactions in a mostly-non-awkward way. It’s possible! I’ve proven it time and time again, since I was a kid and met new friends at the playground!

    • solecism said:

      I’m glad that you found the Captain’s reply helpful, and hopefully many of the comments. Please put the straw man away though–I don’t think anyone asserted that YOU were becoming friends with women as a maneuver to get in their pants. The concern was raised in response to Elysia’s assertion that ZIE “used to buy into the cultural narrative that It Is Best To Be Friends First.” And this hazard is a very real concern for many women, sometimes known as the Nice Guy(TM), as illustrated by xkcd. Please don’t jump to the conclusion that this is meant to apply to you and your situation.

      I can sympathize with the difficulties of initiating conversations that might lead to romance and sexytimes. Unfortunately, the only real solution to possible panic is time and practice (ie, experience that engenders some degree of self-confidence). Role playing and rehearsal can help, along with low-stakes internet dating. Another way to make it low stakes is to start by inviting a very small group (3-5 people) to a group “date” to some sort of fun activity. It gets you into the habit of asking people out without the pressure of a one-on-one situation. If you make inviting an interesting new person to these group “dates” part of the process, that’s one step closer to inviting someone out on a solo date. And these activities may open the door to someone asking you out on a date too.

      • human said:

        “Please don’t jump to the conclusion that this is meant to apply to you and your situation.”

        Um, this is a comment thread about the LW and hir situation, so in this particular case that is a reasonable assumption. Amanda was responding to Elysia, yes, but Elysia was wondering (politely) if the Friends First cultural narrative was part of the LW’s problem.

        And a number of other people pitched in objecting to the broad brush Amanda was painting with. The LW is not alone in hir response to that comment. Nice Guys are irritating as hell, but I do not think the evidence is there to conclude that the LW is acting like one.

        • DBegh said:

          OT, but this is why I think we could have an open thread here on Captain Awkward. A thread where people could share their stories/theories/lolcats/whatever without the risk of derailing a conversation about a LW and their problems. I know sometimes the Captain is very busy and doesn’t have time to answer any letter. Maybe it would be a good moment to introduce an open thread?

          • JenniferP said:

            When I want to read nice people I like chatting about nothing in particular, I go to Twitter. Consider creating a hashtag there and having a discussion and/or having an open thread on your site!

          • DBegh said:

            Oh well, I’m not really into twitter. But no problem, I’ll be fine.

        • solecism said:

          I agree there’s no evidence to suggest LW is acting problematically. And yes, this is a thread that started with the LW. But quite often the comments entail larger conversations that are sparked by the OP but don’t necessarily directly relate to it or the LW in particular. I am simply pointing out that nowhere does anyone suggest (Elysia politely phrased a question, based on hir experience) much less assert as definite that the LW is guilty of such behaviors. The LW was sounding quite upset and hurt by some of the comments. It’s easy to take things personally when they aren’t, and sometimes it’s helpful take a deep breath, pause, and reconsider. I apologize for coming on too strong and possibly adding to the hurt.

          • JenniferP said:

            Re-reading the comments and the letter, I feel like Elysia was calling into question the idea that you should try to become “friends first, then more later” which CAN lead to Nice Guy/Gal-ism if taken to the extreme.The Letter Writer says “the problem is getting from being friendly to being physical” and repeatedly refers to the idea of “more” which implies there was “some” in the first place which could mean that he is trying to or wanting to bone his friends, and it’s not completely out of the blue for her to pick up on that. He’s since clarified that’s not what he meant, so, cool. One of the problems that (many, many) Letter Writers have (see #230 for an example) is that they think that asking someone out is like planning the D-Day invasion and that once you ask someone out you are now committed to date them and OMG, what if you don’t like them that way once you get to know them and and you asked out the wrong person (plus the entire friend group will be RUINED!)? If you build it up that way, OF COURSE rejection is going to seem awful and it’s going to feel impossible to casually ask someone out. I think many people who self-identify as shy and awkward would benefit greatly from a) casual dating that b) does not really go anywhere except “you met a nice person who is not for you.”

            Some people do start as friends and warm up to the idea of romance over time.
            Others do not. That was never in question. It’s so situational, you guys, and depends on the people involved and the feelings at stake, which is why in the letter I suggested expressing feelings “as soon as possible after you feel them” …whenever that may be. It’s the hanging out and harboring without speaking up while your sense of worry/entitlement/evil schemes grows and grows that’s the problem, not the feelings themselves or their timing.

            I say over and over again, if you read this blog and think “She is not talking about me and my exact situation, therefore, I AND EVERYONE LIKE ME AM BEING SILENCED AND EXCLUDED I AM HURT LET’S FIGHT” (vs. saying “Hey, my experience is different, let me tell you about it and maybe it will be useful?”) you should consider reading a different blog. It’s exhausting to qualify every statement with “YMMV” or “Unless this doesn’t apply to you at all” when people are perfectly capable of using their critical faculties.

            Let’s close this particular branch of discussion (NiceGuyism, friends first vs. jumping right in).

          • Elysia said:

            (Captain, I was away from my computer – I know you want to end this topic, but if I may respond?)

            Y’all, the Captain is right about the “friends” and “more” language catching my brain. LW, I’m glad that you clarified, and if my comment(s) hurt you, I’m sorry. I just wanted to offer that figuring out *why* I was anxious about dating helped me reduce my anxiety, and for me, that involved rejecting some societal messages as Inflexible Rules for Elysia’s Life. I have generalized anxiety, so I know that not everyone can get over their weird gut feelings “just” by practicing doing scary stuff. IF you, LW, or other readers, are helped by hearing that, cool. If not, cool. Either way, I sincerely wish you the best of luck.

    • Greg said:

      That have pills for that feeling. If you’re experiencing irrational uncontrollable anxiety that’s impossible to overcome, you may just have an untreated psychiatric problem. It might be worth talking to a psychiatrist. It’s normal to be nervous, but it’s not normal for nervousness to be paralyzing.

      I didn’t even know I had a social phobia until I was on medication for something else entirely, and I noticed the experience of seeing someone I knew at the end of the hallway and not knowing when to say hi stopped terrifying me.

  11. karinacinerina said:

    Fabulousity!

  12. AnthroK8 said:

    I really appreciate when men are gracious about being rejected. Not that I should be giving cookies for decent behavior or anything. But guys who take a “no-thanks” graciously affirm the idea that people can be awesome, and awesome people sometimes aren’t attracted to other awesome people in the same way, and it’s okay, and NBD, and it’s just dating, not peace negotiations in Syria.

    Guys who take rejection well frequently come off looking some combination of grown up, classy, polite, self-confident, or self-aware. Those? All good qualities. Really good qualities, actually.

    Also, men who don’t go for super-contorted, indirect, angling fact finding questions, but choose simple, direct, non-demanding language? Also frequently look like all those things above, because they are taking responsibility for their end of the communication in the deal and not making me read minds. It helps out the other person, if the other person is also nervous/unsure.

    Being classy, grown up, accountable, and responsible? Much more important in the long run than batting .1000 in the asking out and kissing department. Also, with me? More likely to put you in the successful batting column anyway.

    • Admiral Backward said:

      There seems to be an idea that the best way to approach someone is by pretending not to be interested. Isn’t actually being excited about dating someone a good thing? And isn’t it natural, having been excited, to be disappointed by rejection? Obviously it has to depend in part on how the emotions are conveyed, but it’s still odd, and something I’d like to see the Captain address. Here’s one take on it: http://brokenwisdom.com/youre-doint-it-wrong-dating-advice-why-nice-guys-will-never-ask-you-out/ (which I’m not endorsing).

      Batting .1000 is much better than what the Captain’s 1 for 70 (.014), but still not good. I have to wonder how much the percentages differ between in-person and online. Enormously, I think.

      • JenniferP said:

        Admiral Backward:

        Percentages? Really?

        I have addressed the question of “showing interest.” Show interest! The entire post, above, is about how to directly show interest with words and deeds.

        That post you linked seems to be asserting that Nice Guys have better, purer emotions than other dudes because they fixate on one girl and then keep their emotions inside because of fear. Why did you link it? What about it rings true for you (even though you’re not endorsing it)?
        A lot of it, frankly, sucked. I don’t date assholes or terrible men. I don’t complain that nice men date “skanks and bitches.” I want shy people (of every gender and orientation) to get past the idea that rejection means WOE AND PAIN and accept it as normal, so you might as well speak up.

        Back to percentages, who gives a fuck? The world didn’t owe me a lover, and I didn’t owe 50-odd people an hour of my time in a dive-bar or a cafe to make really, really sure that they weren’t for me. Most of the people who wrote to me were just fine. They didn’t do anything wrong. There’s nothing they could have done differently. My picky subjective heart and loins just didn’t want them, or the timing was off, or whatever until it wasn’t. I didn’t feel REJECTED by people who didn’t write me back or want to go out with me, it was just, whatever, that person is not for me. And when someone was for me? My emotions worked just fine. None of the “Rejection Math” part of the post was a complaint – I had a good time meeting people over the past few months and feel very lucky and happy.

        That’s why I say get over the idea of REJECTION as some giant failure. Most people don’t want you. Everyone’s gonna get rejected sometime.

        You show up in every thread on this topic to tell me that I’m not addressing something/should be addressing something. Once again, I ask you: What is it that you want, and can you put it in the form of a question and send it in the emails?

        • Admiral Backward said:

          I swear I’m not trying to push your buttons. Wow.

          That post came to mind because an angsty friend on Facebook just posted it, but I won’t waste anyone’s time trying to defend any piece of it.

          I come here because I value your advice. Sorry if I can’t always encapsulate my thoughts in emailable questions.

          • Admiral Backward said:

            Actually, I just figured out what question was lurking under my posts. And I realized why it’s a really stupid question. Thanks.

          • JenniferP said:

            Care to share what it was?

            I think you and I have communication styles that just don’t gel.

      • DBegh said:

        Yeah, I don’t really understand what was the point in linking to that Nice Guy’s™ “dating advice”. I mean, it’s the same old crap we’ve read all over the internet. “Men who ask women out are by definition assholes!” Since apparently the only conclusion you can get out of a rejection is that you’re not “bro-ish” enough!

        Sigh. These aren’t even NEW stupid arguments.Total waste of time.

  13. nac said:

    I really liked this post. I feel like my situation is very similar to the OP, and while I agreed with all most all your advice, I would just like to say, in my opinion online dating would probably be a terrible idea for him. I also consider myself a fairly attractive and well-socialized guy with a minor self-esteem problem and a month of messaging women on OKcupid and getting not a single response of any kind turned that self-esteem problem into a legitimate depression that lasted several months. Reading profiles of lots of interesting and attractive people who will then completely ignore you is not a good way to get more comfortable in the dating world. It’s a good way to make you feel terrible about yourself, and that’s about it.

    I realize this isn’t everyone’s experience with online dating, and maybe I was just doing something horribly wrong, but I felt the need to offer a conflicting perspective. It’s definitely not for everyone.

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