How can I tell a friend I am interested in pursuing more?

March 14, 2009 3:18 PM

How can I tell a friend I am interested in pursuing more?

I feel like a flipping 5 year old asking this question, but, here goes….

I’ve been friends with a guy for the last few years – at first, a casual friendship and we only spent time to together a few hours a month or so. Well now I spend a day a week with this person, we go out to dinner and get a few drinks afterwards, probably 1x/week. From the time that I first started getting to know him years ago, I would occasionally have a crush on him. For the last month or so, it has morphed into full-fledged limerance/obsession.

At minimum, I would like to go out on a date with this guy/or take it beyond friendship. I know that if I break this subject with him and he is not interested, I will be very embarrassed for a while and I also have a fear of ruining this friendship. I’m an extremely shy person and would not even define myself as a people person (it is hard in general for me to deal with people). In the past, I haven’t had to show any initial interest in a guy in the past because usually the guy makes some sort of move.

Any suggestions for a low risk conversation to let him know that I am interested in more? Or other suggestions? Throwaway email [e-mail]

posted by anonymous to Human Relations (13 answers total)

You go out for dinner and drinks at least once a week? That sounds pretty date-y to me, I don't know that you need to ask him to go on a date with you. Have you tried putting some physical moves on him? I would suggest it. Maybe try kissing him after dinner and drinks some night. Then, if it goes poorly, you can just say, oh, must've been all those drinks, and that'll be the end of that.
posted by ThePinkSuperhero at 3:30 PM on March 14, 2009 [4 favorites]

Based on sketchy info, I'd guess there's a fair possibility he's in a similar situation - interested, but too shy to make a move. Hard to say without knowing him.

I think TPS has a pretty good suggestion - try something small - a kiss on the cheek, or a little snuggle, and see how he responds.
posted by Salvor Hardin at 3:35 PM on March 14, 2009

How about asking him: "How can I tell a friend I am interested in pursuing more? By the way - the friend is you."
posted by 2oh1 at 4:39 PM on March 14, 2009 [1 favorite]

good advice above - I'd try this: at the end of the night, as you're saying goodbye, say "you know, I really enjoy our time together" say it happily, with a friendly smile, and then give him a hug - the way he responds to the hug should tell you a lot
posted by 5_13_23_42_69_666 at 4:41 PM on March 14, 2009 [2 favorites]

"hey, we seem to get on pretty well - what do you think about dating?" - this approach has the advantage of making your attentions clear, without being too heavy.
posted by cogat at 4:44 PM on March 14, 2009

There isn't a low risk way to do this. There just isn't. If you're going to go for converting a friendship you risk a sort of rejection that's particularly painful and you also risk putting a real strain on the friendship. The potential rewards? Hey, I've been married to my friend for over 7 years.

This being said, the minimal facts you present are in your favor. Pick a private venue and just say how you feel.
posted by nanojath at 4:52 PM on March 14, 2009

I actually wonder if the routine of date-like outings once a week might make it even more important to be explicit. I mean, not to say that making a move physically would be a bad idea, and it could well be that he's in the same mental/emotional place as you, but I think it's equally possible that it wouldn't occur to him that you should date because you get together on (to his mind) totally platonic date-line outings so frequently. If a stranger or new acquaintance of your preferred sex/gender asks you to dinner, you probably assume it's a date; if a friend asks you to dinner, you probably assume it's just dinner with a friend--meaning you need to be super clear if you want it to be anything other than just dinner with a friend. So, I prefer cogat's approach to ThePinkSuperhero's, but obviously you know him better than any of us.
posted by Meg_Murry at 5:18 PM on March 14, 2009

I just tried this exact thing. And I was turned down. But you know what? I feel soooo much better about myself. Liberated even. I totally swung for the fence and I ended up with what I had before I stepped up to the plate: my best friend. Right there, still supporting me. Yeah sure, it hurt that she did not feel the same way, but in a lot of ways, it opens things up.

Oh, here's how I did it: I fashioned a card with my feelings, but then I just told her, after a movie. Then I gave her the card. She was floored, but yeah, it's o.k. It's better to take that risk, then to never know. Good luck.
posted by captainsohler at 5:22 PM on March 14, 2009 [1 favorite]

I thought this answer was quite good.

You just have to tell him, but if you have some kind of joke lined up that you can crack if you get turned down, hopefully you can imply that it's not a big deal, and circumvent the embarassment/awkwardness and go straight back to friends.

Or yeah, have a few drinks, bust a move, and if it doesn't work out you can blame it on the booze.
posted by Emilyisnow at 6:17 PM on March 14, 2009

this is why the good lord gave us alcohol
posted by swbarrett at 6:32 PM on March 14, 2009 [1 favorite]

Kiss him.

This came up on AskMe a bit ago. "Kiss her and find out" was the consensus. Then we got a follow-up telling about how they're a couple now.

It's better to try and find out than to not try and always wonder.
posted by dunkadunc at 3:44 AM on March 15, 2009

Do what TPS said, or just tell him. I came to AskMe with a similar question, and that was pretty much the advice I got. I got turned down, but dealing with it directly improved my quality of life dramatically.

Also, thanks for teaching me the word "limerence." That was definitely where I was headed when I posted to AskMe, and I think it's good to head it off at the pass, as it were, than to let it take over because one lacks the courage to just get out there and say it.
posted by ocherdraco at 2:33 PM on March 15, 2009

Yeah, don't ask, act.

After drinks, hug him goodnight and kiss him on the cheek and then look in his eyes and hold it for a second. Hold it for longer than you should. If he doesn't look away or break it off, embarrassed, kiss him.
posted by Potomac Avenue at 5:39 AM on March 16, 2009 [1 favorite]