Should I date my friend or not?

We've been in the same friend group for years but really haven't spent much alone time together at all. I was told he's had a thing for me for a while now, and since I just moved back to my hometown he's been pursuing it a bit more actively. Hasn't full on asked me out yet, but I can tell he's working his way up to it.

So I'm faced with a dilemma. I like him well enough. He's a good guy. He's pretty darn attractive. But I don't know.. the few times we've been alone together, we had a hard time finding stuff to talk about. I'm not sure we have much in common. He's really fun to hang out with in a group, but when it's just us it's, I don't know, less comfortable? Slightly awkward? Struggling to keep the conversation going? And the risk is high because we're in the same friend group. Our mutual friends are married to each other. If we started dating and it didn't go well, I worry it'd make hanging out weird.

Feel free to weigh in. Give me all your thoughts. I want to think this through from every angle. On the one hand, I don't want to turn down a perfectly decent guy. On the other hand, I don't want our friend group to turn awkward (I'm distinctly bad at dating lol, I just get nervous and clam up). There's a million ways it could go wrong and only a tiny chance it'll be amazing.


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Most Helpful Guy

  • If you have had trouble getting along one on one in the past, it will be evermore difficult if you're on a 'date', and chances are your friends are waiting to hear about it from one or both of you.

    There will be more pressure now that previously. And it didn't work well previously, as you describe.

    I'd explore what he's thinking while you're still going out in a group, and also ask the other people what they think of him. Stay distant for now until you get reassuring answers to your questions.

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Most Helpful Girl

  • I did that and when we broke up after 3 years, I lost many of my friends. Now, every situation is different, but I wouldn't do it again.

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Have an opinion?

What Guys Said 13

  • Yes and it sounds like it isn't going to work. But if you don't try, then you'll never know nor will you grow.

    Distinctly bad at dating - the way to get better is date, study, learn, etc.. Find some subjects to talk about in advance and let the discussion roll. If it doesn't, then he cannot lead yet, isn't ready to date, or it isn't a good match. Talking is like... the most basic function. It'll get tougher than that...

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  • Well, this is a difficult situation because he's obviously shy. It seems you are a bit as well, which makes it slightly more complicated.

    The general rule I like to follow is, if there is a hint of chemistry, go for it. NEVER trick yourself into thinking that there is something there that isn't. Don't just say to yourself "well we're both single so why not?" unless you are looking for a lay.

    In this case, if you feel that strongly that something could happen between you, then make a move and invite him out. if nothing sparks, then just leave it and move on. there's no time to play games and if he felt that strongly, he would close in.

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  • Go on a date with him. If things turn out well , your life will be settled. Other wise it will just be a minor setback if he rejects your offer. Your friendship may or may not be different thereafter if he rejects you. But taking a minor risk to get a big reward is a worthwhile proposition.

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  • It sounds a little force tbh.. You two are good as friends and should remain that way. I just don't see it going anywhere else since you two don't have too much in common and the silence and awkwardness being alone together pretty much says it all. Good luck :)

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  • You need to find ways to be comfortable with each other. He is also probably nervous. If you go out, do something childish and awkward. Be patient and forgiving, and encourage him to be that way. If he feels like he said something stupid or is embarrassed, reassure him that everything is all right. Imagine you did the same thing and how would you want him to react?

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  • hey.. have you seen how I met your mother?

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    • Show All
    • There are exceptions. But if they never even went out, it was probably easy for them to stay friends. It's not like they dated for a few months and then broke up.

    • they were real close and it was the first time the girl proposed.. and the first time.. the guy ever got proposed..

  • Follow your gut. Everything you've said makes me believe that dating him would be a bad idea.

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  • just hang out casually and go from there. no labels, or a date. just see how it goes from there. if you say no right now, it seems like you're dismissing it before he had a chance.

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  • Yeah give it a shot, you guys may have a good time and really click or worst thing worst it doesn't work out and you both move on with life and live another 50 years

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  • what do guys like to do? video games. even if you don't like that crap it'll probably put him in more of a relaxed state to communicate. just a thought

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  • It's all up to you. Don't care about what your friends think. If you like him, date him

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  • Just give it a shot. If nothing is working afterwards then it just wasn't meant to work out then.

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  • do what you want fam

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What Girls Said 4

  • I would stop the anxiety and you ASK him out FIRST!

    Then just because you are friends, it doesn't mean you can't be more..

    Instead of you 2 trying to find a conversation topic, when you get alone, tell him you know he has had a crush on you for forever, you like him a lot, but are afraid of ruining your friendship... THEN lean in and kiss him...

    If the kiss goes alright, take the next step and make out with him for a couple hours.. it doesn't have to be sex, but do what feels right.

    Some of my gfs have married the guy that was just the "guy on the edge of our group, so and so's brother" that they never thought was date material, but once they went past that point, LIfe was magical.

    Just my 2 cents worth...

    Nothing ventured, nothing gained...

    Those who dare, win...

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    • Good advice but for me I think the kiss and make out part is early but heck why not 2 people like each other God for it

  • I would say to go with your gut. If it just isn't clicking when you have had alone time (which is how it sounds), then I'm not sure that more alone time would improve it. Unless maybe you think it's because he's shy (or you are) and you think that y'all could eventually get over that. Otherwise, the cost/benefit analysis as you have described it makes the costs seem to outweigh the benefits.

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  • I can't say I have been in this situation before but in my opinion I think it is better to take a risk then to regret never taking the chance later on. Yes, if you guys break up then it might cause friction and tension within your friend group. At the same time, if you guys end up staying together for a long time, your friend group might grow even closer.

    It's a tricky situation! I hope I helped in some way and I wish you good luck in whatever you decide to do

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  • This seems like it's too forced, it can only turn out badly.

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