Hey Cap, ive got some girl troubles i hope you can help me out with. So a couple years ago i got the pleasure of meeting a girl, me and her would hang out almost daily and we became very close, we were extremely flirtatious and everbody thought we were together. But a few months into our friendship our communication went a little cold and we stopped talking for a little while. I then had a brief relationship with someone, and so did she. Its now a year later and we have been hanging out again and i brought up the courage to ask her out. If i would of done this when we were closest back then it would of been an instant yes i believe. But now she is really hesitant, scared of being hurt, and losing me as someone she can talk to. I want some cold truth here should i keep trying or move on?
Thanks!
I’m so sorry that you seem to have missed the window on this one.
You saying “Hey, I’ve always really liked you and I’m glad that we were able to get back in touch. Do you think we could give dating a shot now that we’re both single?” is brave & cool. There’s absolutely nothing wrong with saying it, and there’s nothing wrong with her hearing something like that from a good friend and needing some time to process and perhaps mentally reframe things a bit before committing one way or another. I think the smart thing for you to do now is to treat anything less than “Hell yes!” as “No, thank you” and give her some space. “I had to ask, I only want you to say yes if you feel 100% great about it, so why don’t you think about it and we’ll talk in a few days/weeks/whenever you like.” Giving her and the whole matter some space will be good self-care and good care for the person you like.
It’s also a good tactic for getting to the heart of the matter. If she does like you back, if she is just sort of processing doubts aloud because she wants to be convinced, I think it’s good for you to bow out while she comes to her own conclusions and refrain from trying to convince her. People don’t forget being asked out by their friends, phones and email work both ways, and if her answer to your question a week from now is “You know what, let’s go for it,” she knows how to find you. You being respectful of her reservations isn’t going to lose you any points if this thing is meant to be, and if it’s not meant to be bowing out gracefully is a way of assigning yourself some grace and coolness points even in the middle of something that feels sucky and awkward.
CaptainAwkward.com 
Agreed with the Captain. Since you’ve brought it up once give her space and don’t ask again. Nobody likes to be pestered into dating.
Very true advice, and remember… women talk. Even if she decides it’s a no, if you’re cool about it there’s a non-zero chance in the future that she might communicate to a friend “Yeah, LW was really respectful and awesome this one time when we talked about maybe dating. I would totally endorse LW on the LinkedIn of dating even though it wasn’t right for us.”
Which, obviously, that shouldn’t really be your only motivation for respectful behaviour, but I think “being good to people reflects well on you” is usually a good thing to keep in mind.
How much space are you recommending though? Like, just on that one issue. Because it sounds like you mean to leave her alone until she makes up her mind.
A guy dissapearing after not getting yes to a date is almost as bad as one who keeps asking.
“A guy disappearing after not getting ‘yes’ to a date is almost as bad as one who keeps asking.”
I’m not sure I can agree with that. However, a guy pretending to be a friend in the hopes of getting attention or a date (i.e., a “Nice Guy™”) that then disappears after being told no to romance/sex was never a friend to begin with. Good riddance, I say. Someone who sincerely wants a date and is told no isn’t obligated to maintain contact out of politeness.
I’m confused. If he IS in fact a real friend, wouldn’t that make disappearing super awkward? Would for me. That would falsely advertise him as “pretending to be a friend,” even according to your comment.
There is some hairsplitting going on here and I don’t know who started it but I’m ending it.
If LW is a real friend and these two are going to have an ongoing friendship, disappearing completely and dramatically after a romantic rejection is not cool, but taking a couple of weeks to lick wounds and reset things is cool. If my friend says “I think I might love you” and I say “Nope, sorry,” I’m not going to expect that friend to immediately default to being my inseparable buddy & #1 feelings processor as if nothing happened. In that case I’m gonna give it a couple of weeks and then ask them to do something low-key, probably something with some other people around, probably something that has a defined time limit and something to do besides talk like a movie or a show so that everyone can ease back into a comfortable place. Other people might have a different idea of what giving space means or a different way of handling it and that’s okay.
If LW’s main goal in being friends is to eventually date and there isn’t anything to sustain the friendship if that’s not gonna happen, it’s actually perfectly okay to fade away after a rejection. The person with the crush will have the sting of rejection, the person who did the rejecting will have the sting of “hey a friendship that I thought was just a friendship was something else and now I feel weird.” All of those weird feelings are way more survivable if you don’t fake it! Say a polite hello when you do run into each other and otherwise don’t make an effort to interact. If you’re meant to actually be friends, common interests and social connections will bring you back into each other’s paths without anyone having to try to make it happen. Time will make it all less awkward.
Uncool: Saying you are perfectly fine with staying friends when you aren’t and really just want to keep convincing or maneuvering the other person into a romantic relationship.
Friendships can mostly survive awkward crushes & rejection. Fake friendships that are only about the crush mostly can’t, and that’s not a bad thing.
Ack! I have a comment in moderation. Seeing your post here, please delete it and kill it with fire as you said what I tried to say only much better. 🙂
Eek, too late! We passed like ships in the night. Also your post is good.
Is there any room here for the guy to pull back while they process their own disappointment?
Clearly there has to be, since the alternative is sheer misery. Lots of commentors are making that point.
One thing the LW should be aware of is that there is a strong potential here for miscommunication. What LW perceives as briefly pulling back, setting up boundaries, looking after themselves, may be perceived by the woman as a sign that maybe the friendship was just a pretext. LW can try to say what’s going on in their own head as clearly as possible, but also realize that it’s impossible to determine how the other person is going to respond.
I disagree with this. If someone has unrequited feelings, it can be a very healthy thing to pull back. People aren’t robots and they cannot shut off their feelings–and being around the person you are into isn’t going to help you get over their rejection of you. If it’s awkward or painful I don’t see why it’s such a bad thing to distance yourself. Especially if the friendship had flirting in it and people assuming you were dating. That would be a mind-fuck.
Not sure I totally agree with this, but I also don’t think it’s unreasonable, if she rejects LW, for LW to say “Okay, I’m disappointed but that’s cool. I think I’m going to take some space to process this and reset my hopes/expectations of our relationship. I’ll check back in a little while/few weeks/insert-time-period-here.”
Exactly. You don’t have to disappear with no explanation! Tell her what’s up and check back in later.
The Captain is right on the money. Sadly, and I hate to be so brutal because it’s happened to me and I know what it can be like, there is a good chance that she is trying to spare your feelings by saying no in a nice, not too abrupt way. However, of course there is also a chance that she intends her words to be taken at face value. Fortunately for you, the course of action to take in both cases is identical: Do nothing, and continue to treat her as any other friend. If the lady in question is really thinking about it and might end up on the side of “yes,” then the best way to kill that and push her right onto the “no” side is to pester her, drop hints or outright ask her again. If you did that, she would almost certainly be put off completely.
I know that it might be hard to hear this, and when you’re crazy about someone it can be so hard to do nothing and often even feels like you’re living a lie by hiding your true feelings from her. But as the Captain astutely pointed out, you’re hiding nothing because you have told her (your friend, not the Captain) how you feel and she isn’t about to forget that.
Your priority must now be yourself. Look after yourself, because these feelings of uncertainty and wishing things turned out differently can be really uncomfortable to live with. If you try your best to distract yourself, not only is that great for you but it’s also great for giving your friend the space she needs. Immerse yourself in hobbies! Take up something new! Maybe go for long walks if you can. Make time to get back in touch with an old friend you haven’t connected with for a long time. Do whatever makes you happy but doesn’t involve the friend you have strong feelings for. I’m not saying ignore her, just let her initiate the next contact you have.
If someone had given me this advice when I was in your position, I think things would have turned out a lot better for me! I made the mistake of trying repeatedly to “explain” my feelings to this person. He didn’t want to hear it and ended up feeling guilty that he couldn’t give me what I wanted because he didn’t feel so strongly for me as I did for him.
All the Jedi hugs if you want them! Unrequited feelings are not fun. Good luck!
“…and losing me as someone she can talk to.”
If she doesn’t like you back the same way, she needs other people on her team to be this person. Her rejection will probably hurt, so take care of yourself by NOT BEING THAT NICE GUY ™.
I have 2 stories related.
1. I told a guy I liked him, he declined my interest but kept up the friendship in the same manner as before. I wish I’d stepped back and let that crush die instead of hanging on to it for another 2 years.
2. A guy told me he wanted to date me. I declined, but the next day I initiated talking to him so I could take it back and say yes instead. Now we’re married.
Step back. She has your number.
Very good advice from the Captain here! The best thing to do right now is let her figure out how she feels without being pressured.
The only other thing I would add is a little advice for if she decides she doesn’t want to date. If that’s how it goes, it’s totally normal for you to have sad, disappointed, etc., feelings about that. You may find that, if she turns you down, it hurts to spend a lot of time with her. That would be totally normal! It hurts when we want a different or closer relationship with someone than they want with us. If that does turn out to be the case, I want you to know that there is nothing wrong with deciding to take a step back and spend less time with her while you heal. In fact it is a great way to take care of yourself! Sometimes we need to get away and lick our wounds for a bit, and then we can continue forward with a friendship. It’s also ok to set boundaries with her about what your friendship looks like going forward: you don’t have to be her sounding board for boyfriend troubles or continue being “extremely flirtatious” with her if that kind of thing is going to make you uncomfortable or upset. These can be REALLY HARD boundaries to learn how to set, which is why I wanted to give you the heads up. Probably most of us here have been in a situation like that on one side or the other (or both) and it is painful and awkward for both people. I have been there more than once, myself, and it sucked every time.
Anyway, perhaps she will decide she wants to give it a go, and my advice will not be necessary right now after all. Whatever happens, I wish you the best!
Yes, this is the moment when it is so tempting to be not only a continuing friend but AMAZING FRIEND because you’ve shared this difficult moment and you were cool about it, and look how that has drawn you closer! It can feel really intimate and why can’t the other person see that it means you are great together?
Sadly, your being an awesome very close friend who gets the other person does not give you the right to a chance romantically. It can be painful to come to terms with that, so it’s helpful to have some space after a rejection to reset the boundaries. Because it is a little painful and confusing (sometimes more) to have the person who rejected you also be the person who feels free to call you anywhere, anytime and then have it not turn romantic ever. Don’t promise to be that person right away, at least. Maybe a year from now, you will want to be that kind of friends.
This is fantastic advice.
There’s always the chance that the space you give your friend that is a girl (and not a “girlfriend”) may turn into silence, no response, and no further contact. At that point, the answer to being your “girlfriend” girl friend is officially “no.” In that instance, exercise great self-care, allow yourself to mourn what might have been, throw yourself into other “non-her” activities, and look for love in other “non-her” places.
There’s also a chance she might say yes, but from your letter it looks like that chance is very remote. In either case, always exercise great self care and don’t give up your “non-her” activities. All the best. ☺
I would only add that it’s best not to torture yourself with “if only I had asked her a year ago, she would have said yes”. To begin with, you don’t know that at all; and, even if it’s true, it’s not helpful to dwell on that thought.
Agreed! And those forlorn “what ifs” can fester into resentment. Things progress and people change. What you wanted years ago is seldom what you want today. There’s no point in pestering someone why their favorite food is no longer pancakes when it was clearly pancakes for that one summer three years back.
You are correct.
It almost certainly isn’t true.
There was a boy who liked and liked 14 year old Morley. 14 year old me didn’t like him. Nor did 15 year old, 16 year old, all the way through now Mrs Morley. None of his reasons that I should have liked him were tied into me. They were all his own thoughts and assumptions.
LW, don’t be like that boy. He carried a torch for five or six years.
There is at least one person in my social circle who, I’ve been told by a reliable source, believes that if I’d met him before my boyfriend, we would be dating.
Problems with this:
I met him through my boyfriend, so if I weren’t dating BF, I probably would never have crossed paths with him, but also:
I’m in an open relationship. Monogamy is not what’s holding me back from letting him touch my boobs, which leads to point three:
He’s a nice enough dude, but I’m not into him. Yes, being with my current partner has set some of dials to certain places, but it didn’t completely reset my OS, so to speak.
Omg. What a brilliant comment.
Hi, LW. I have been where you are and it sucks, no question. I’m glad you said something, I think that is great.
And now I’m going to say, as someone who’s ALSO been in your friend’s shoes, that you need to let it go. Being pestered and nagged by someone who doesn’t hear the no is frustrating and off-putting–a friend has been doing this and we are no longer friends. You cannot–and should not–talk her in to being your girlfriend. She knows how to get in touch with you if she changes her mind. The ball is in her court–if you “keep trying” you’re basically not accepting the no.
I also want to echo the advice to dial things back and set some boundaries. It sounds like there was a reset after things ‘went cold’ anyway–which may be why she dropped out for a while. If there is flirting going on it’s okay–and very advisable–to put the brakes on that. Ditto for confidences about dating woes, etc. And there is nothing wrong with giving yourself some space from her until you’re over this.
Also, I’m seeing some pushback against the idea of taking space after a rejection:
I think it is a fine and good thing to give yourself some space from the person who rejected you. You’re hitting the reset button and that’s a wise thing to do IMO. I’ve done it. It didn’t mean that I had no feelings for him or that I was a terrible friend. I just knew that continuing to hang out with him at the frequency I did would not alleviate the situation, and would keep me from being emotionally available to meet someone else who *would* be interested in me. It beats torturing yourself. I have been on both sides of this and when I was the one who didn’t reciprocate romantic feelings, I would have felt sad at not seeing a friend, but I would have understood.
I’m now dealing with someone who decided to ignore my no’s, nag me, push gifts and favors on me that I have repeatedly and clearly declined, and basically drive me as far away from him as I can get. Had he taken space for himself or just plain stopped hanging out as a friend after I said no to dating him, I would not have the bad feelings towards him that I do today. I had taken some space after that and he got very hurt, so I figured he was okay with being just friends. Nope, as it turns out, as I got unrelenting pressure. I have cut off all contact and do not consider him a friend anymore.
Also, it’s not the LW’s problem if their friend has an issue with them taking some space or hitting the reset button. Frankly, I’d rather they do that than nag and hector her into dating them. From what the letter says, they were close for a few months and then things went cold.
Oh LW, you are so brave and cool!
Tried to date two of my friends this year! Initiated both conversations.
Story 1: Had a flirtatious and close friendship with a person a couple years ago, moved away, and then he ended up moving to my city for unrelated reasons. I brought up the possibility, we agreed it was a bad idea to date, but that we were attracted to each other, did sexy things, decided it was a bad idea, and after a few weeks of awkwardness went back to being good friends.
Story 2: Was visiting a long-distance friend I’d liked for a while, said “hey, have you ever thought what it would be like if we dated?” Friend was confused, followed by agreement that dating might be a good idea if we were in the same city but that it couldn’t really be an ongoing long-distance thing. I said that was absolutely no problem, and we had a lovely two-day romance and parted ways. I tried to forget about it. He changed his mind a few days later and asked if we could try to date long-distance. Still trying that, working out well so far!
LW, if your friend uses your previous close friendship to try to rules-lawyer you into being her sounding board or jumping back into a close relationship before you’ve had a chance to move on from your romantic feelings, don’t take the bait.
It’s really tempting to hear “Please, let’s stay friends! Nobody else gets ____,” or “You’re the only one I feel comfortable enough with to ___,” as “In time I will admit how perfect we are for each other!”
No doubt, she truly values your time, attention, and affection. But you deserve time to mourn the romantic relationship you wanted. The idea of feelings as a continuum that people can dial up or down at will leads to a lot of heartache.
Dear LW,
I’m sorry that her answer seems to be no.
But to answer your question: No. Do not “keep trying”.
She gave you a soft no, with a handful of reasons. Do not argue with the reasons; recognize that she gave you a no.
(What do you think “keep trying” would look like, honestly? “I know you gave me a lot of reasons you don’t want to date me. But I want you to, so I’m going to nag you about this! Maybe you’ll give in” is about as nice a framing as there can be.)
If she changes her mind about that, she can let you know.
Meantime, you were brave, and thank you so much for stopping to get a check on this instead of going into the full-on entitled asshole mode of “I will pretend I don’t understand and will pester until I get what I want.”
On the topic of hanging back, I recommend asking your friend how much space she wants. It sounds like you are good friends, so hopefully you can say something like “Hey, now that I’ve put my feelings out there, could you let me know if I do something that you think is inappropriately romantic-y? I don’t want you to be uncomfortable around me. I know I may have changed the dynamic by bringing up my feelings for you, but I want us to be friends.”
(I knew a guy in uni who confessed his crush to a friend. She did not reciprocate, and wanted space. He did not take it well, and spent a lot of time loudly asking people why things suddenly had to be different, why she didn’t trust him to sleep over in her bed any more! Um, it’s because you told her that you smell her hair while she sleeps, dude. She gets to be uncomfortable with that.)
First: D: to the hair-sniffing
Second, I am old, because I immediately was reminded of this:
Tried img tag and failed, so: https://daytodaydetox.files.wordpress.com/2015/03/gee-your-hair-smells-terrific.jpg
LW you are brave and honest and I want to pin a medal on you. I’m sorry it didn’t go the way you hoped it would.
The Captain is wise – if she wants to take you up on it later, she will let you know, but as of now, the answer is no.
And – I don’t expect you to believe me right now, ok, this is for later – that is short-term awful but long-term good, because you deserve to be in a relationship where you ask someone out and they say Oh Hell Yes Please.
So now you get to figure out what she means to you as a friend, and if that’s something you want in your life.
Take some space, don’t take some space, offer her some space, let her make that call herself – really, the important part is the actual honesty. Just go ahead and use your words, whether that’s “ok, I need to take a few days/weeks to be sad about that but then I hope we can go on as before” or whatever.
I’ve been out of the dating pool for a long time, but I discovered something back then that I would keep in mind if I ever hit the pool again. I really prefer to date friends over new acquaintances.
When I’ve known a friend long enough to feel comfortable letting her know I’m romantically or sexually attracted to her, and by comfortable I mean also feeling like she might be receptive and my preference for dating friends has been broached previously, I let her know with a script something like this:
“I like you a lot, maybe more than like, if you know what I mean. I find you attractive in several ways, [list a few, including things that make her a great friend]. I don’t want you to feel like you have to make any new choices; I’m just making my feelings clear. If you’re interested, great! If not, that’s fine too. Either way, I value our friendship and want to keep that.”
Then I basically forget I said anything. If she retreats and wants some space because I misjudged and she’s feeling awkward, I don’t press matters or try to stick to the old status quo; I threw that out when I opened my big mouth. If she just acts like I never said anything, then so do I.
I can’t say I’ve got a long track record for this approach, having taken it exactly four times, but I enjoyed two good romantic relationships, one brief and another longer term, and kept two other good friendships healthy and happy.