How to ask someone out? No, literally, how the hell do I communicate this?

February 16, 2008 2:30 PM

Please help me with my mild relationship idiocy. You see, there's this boy (as always), and I really dig him and I'm pretty sure he really digs me. How do I find out for sure?

I know, I know -- ask him. But how? E-mail feels impersonal and like I'm trying to take the easy way out. We meet up for a beer about once a week, and I'll usually see him as part of a group activity once or twice more in addition to that, so there's plenty of opportunity, and time together. I really, really like him, and I want this to not just keel over in a crush that ends in my own head.

So help -- how the hell do I communicate this? How do I bring it up? How do I do so without seeming creepy or icky, and while staying chill enough that even if he wants to be friends, nothing more, that's cool and he'll know that? Feel free to write a script for me, or something -- I'm really feeling at a total loss here. I don't want to, out of the blue, say "hey, I want to be more than friends"...unless that's not that unusual? It's been a ridiculously long time since I've dated, so I'm a little rusty :)

(Perhaps the question here is, how do I stop overthinking this plate of beans...)

Possibly (?) complicating matters, I just found out I'll be moving to the UK this autumn for school. So, almost by definition, this isn't going to be anything long-term; I'm looking for fun with someone who's really made my life much better in the last few months, and that's a gorgeous thing. If I can ever get it off the ground. He's not a Mefite (as far as I know -- and hey, if so, my problems are solved!), but very much runs in that personality-type, so all your advice is gratefully welcomed.

Thanks!

posted by kalimac to human relations (25 comments total)

Next time you meet up as a group, make arrangements to go out as a couple. Get a bit tipsy, then kiss him. It'll give you Dutch courage, and depending on how he reacts, you can blame it on the drink.
posted by Solomon at 2:37 PM on February 16, 2008

Here's what you do. When you are at the bar, you say "Hey, do you want to go out on a date?"

If he says yes then pursue. If he says no say "Okay" and continue on as you are
posted by Loto at 2:38 PM on February 16, 2008 [8 favorites]

2nd Loto.
posted by shakespeherian at 2:48 PM on February 16, 2008

3rd Loto. JFDI. Less thought, more action.
posted by gaby at 2:50 PM on February 16, 2008

3rd Loto.
posted by lia at 2:50 PM on February 16, 2008

Ok, 4th then!
posted by lia at 2:51 PM on February 16, 2008

The problem with these questions is that we never find out how it turned out....
posted by nax at 2:52 PM on February 16, 2008

3rd'ed

good luck!
posted by andythebean at 2:53 PM on February 16, 2008

What Loto suggests, but add something specific to "wanna go on a date?" Something like, "Hey, do you want to go out on a date? How about dinner and a movie [substitute date activity of your choice] on Friday night?" That changes it from a vague someday sort of thing, where it is the other person's problem to make it happen, to a clear question that needs a yes/no answer.

The best part is that if things get awkward, you are leaving the country soon so who cares?
posted by Forktine at 2:53 PM on February 16, 2008

Oh, man, Loto, you're awesome. (Other suggestions still welcome! I like a variety to choose from :) )

Also, even though I have sucked at followups to askme's in the past, I promise I will update with how this turns out...
posted by kalimac at 2:56 PM on February 16, 2008

Thanks kalimac (I'm just nosy). Good luck!
posted by nax at 3:03 PM on February 16, 2008

Maybe casually invite him home with you after the beer. Tell him about the great movie you just rented that he really should see, that you've got this book you want to loan him, whatever. If he really is into you, he'll probably go.

Then give him an excuse to stay past the original excuse to come over. Ask him if he wants to watch a DVD, show him funny crap you found on YouTube, offer him food. Touch him more than necessary. Give him lots of openings, like mentioning that your neck is stiff so that he can offer to rub it, using him as a pillow during a movie, etc.

If he doesn't take any of those openings, you can just thank him for coming over and let it go without having really risked anything. At least, you've set a precedent, and if he hasn't gotten up the balls to make a move yet, he can now quid pro quo and invite you over to try again.
posted by Gianna at 3:29 PM on February 16, 2008

If you want to add a touch of humor to it, instead of, "hey, want to go out on a date", say "soo... when are you going to ask me out?" This worked on me once. I dug it. Though I was mildly annoyed because I WAS going to ask her out, THAT DAY. I had done the whole pumping myself up for it, and gotten over all the "what if she says no?", "what if I'm totally misinterpreting, and she doesn't dig me?" etc etc. Possibly contrary to common sense, I don't think I'd recommend this on the type of guy who thinks the guy ALWAYS has to ask the girl out. You won't be fooling anybody. You're obviously the one doing to the asking-outing if you use this line. I'd use it on someone, like myself, who may be a bit shy, and who is not too hung up on gender roles. That way he'll hopefully get a kick out of you lightheartedly poking fun at his shyness, and also at the idea that the guy ALWAYS has to do the asking-outing.

Also, in the very unlikely event that you get a big, resounding, "no way. you're crazy. do you really think I was flirting with you?" you'll have a sort of plausible, "uhh.. I was joking too" defense, because, you were joking. Just not about the asking out part.
posted by gauchodaspampas at 4:48 PM on February 16, 2008 [1 favorite]

I don't think email is so bad. I've hooked up dates with acquaintances that way, and worse (messaged them on social networking sites). Maybe it's just because I work with the Internet and hang out on it a lot, but I don't think it's an impersonal thing at all, especially if you're too shy to do something in person and might miss the opportunity entirely.

A short email that says "Hey - how about a date, just you and me? There's a show going on next Thursday - want to go see it with me?" will work just fine. You do know him personally and have spent plenty of time together in person so it seems fine to use email for what it is: a simple communication tool.

Just make sure you use the word "date." You can't figure out quickly and easily how he truly feels. But you can make it clear that you want a date, and find out if he's interested.

Good luck!
posted by scarabic at 5:28 PM on February 16, 2008 [1 favorite]

"soo... when are you going to ask me out?"

True, might work. But this kind of thing irritates me. It feeds into the stereotype that men are supposed to take all the initiative, which is just dumb in my book. It also starts things off on a "you've been screwing up all this time" kind of tone, which may put him off. And it makes you sound pushy - yet you've never taken the step yourself. To be avoided, IMHO, but it does depend on the person and the circumstances.
posted by scarabic at 5:30 PM on February 16, 2008

I would be careful with Gianna's suggestion above. Passive tactics are sometimes read wrong and you end up thinking you got a negative answer when really it was the other way around. Some guys like to play, "the gentleman role," in hopes of showing their worth. Playing games never works in the long run. I agree with those who suggest you just ask him out and see where it leads. Good luck!
posted by Gerard Sorme at 5:47 PM on February 16, 2008

Gianna -- I get your point, and can see how that would work out. Unfortunately, I have a habit of being passive-aggressive that I'm desperately trying to break; flat-out asking the dude out is one of those things that I'm hoping will help break that. I'm willing to lay my heart out and go all-or-nothing and totally honest, as in Loto's suggestion, even if it does wind up with him giving me an odd look :)

(Also, when trying to flirt, I inevitably look like a giant twit. Simple language and small words == my best bet.)
posted by kalimac at 9:13 PM on February 16, 2008

Sounds like you haven't told him you plan on going to the UK later in the year. Tell him about it, and maybe he'll make it clear whether he'd like to hang out with you on a more personal level, or if he'd prefer to be friend. You don't want to lead him on and break his heart by implying you were only looking for a short-term fling.

Plus, on your end, you'd wanna be careful about getting caught up in a relationship that you know will be difficult to sustain even if it starts out well. Think ahead... What happens in the fall if you go head-over-heels for each other now?

That said, e-mail probably isn't too bad. It's not really putting him on the spot, and he won't have to fumble around for words if he's not quite so interested, and you won't feel embarrassed if he turns pale and suddenly avoids eye contact. Just write in between meetings, saying you've really enjoyed hanging out with him, and that instead of the usual drink, maybe he'd like to try something else. Heck, he'll probably be relieved you're doing the asking. Depends on his personality, I suppose.

With this sort of thing, do what you feel comfortable with. If he ends up judging you as too passive or weak because of it, you probably wouldn't want to go out with him anyway, right? And if he does like you, it wouldn't matter in the least what method you use. And if it's somewhere in between and you're not sure where he stands, he might be in the same boat as you, and is too afraid of how he'll come off if his affection for you is too obvious.
posted by TheSecretDecoderRing at 11:08 PM on February 16, 2008 [1 favorite]

Get a bit tipsy, then kiss him. It'll give you Dutch courage, and depending on how he reacts, you can blame it on the drink.

Dammit! I knew all those girls in college were just too shy to ask me out. That's what I get for blaming it on the drink.

"soo... when are you going to ask me out?"

Agreed that this is not the way to go; as someone who once got "why haven't you made a pass at me yet?" I can say that didn't set me up to have much respect for the girl.
posted by davejay at 11:13 PM on February 16, 2008

Just to be clear here (even though this question is answered, right?) - Loto's suggestion doesn't involve 'laying your heart on the line' or any such melodramatic shit. He's describing a simple, indeed an atomic, element of social being at your point in spacetime. It requires no risk. This is simply what people do, and the more we ask - and and accept - the easier it becomes. Since you're not actually living one of the Bridget Jones novels, it doesn't matter what interior drama it takes to get you to pop this rudimentary question.

And asking someone on a date isn't 'honest' in any big way. It's like asking someone to grab a beer after work, only there are only two of you. You can manage expectations past that point (i.e. if you want you can simply let the dude know if the making-out and the good-foot-bad-thing are in the cards).

You're asking for help with this because you feel it's in some way a hard thing or a big deal. Loto's answer is not only correct in substance, it should illuminate for you the broader concern that by interacting with people in this simple way you are taking part in a very basic system of interactions.

If it doesn't go off, tell the bartender to leave the bottle and make a MetaTalk request for DateMe. I'm sure Matt's already got a prototype coded up anyhow.
posted by waxbanks at 7:25 AM on February 17, 2008 [1 favorite]

Heh. Thank you all for dragging me back to earth -- I did get a bit melodramatic there, didn't I? What waxbanks says is important -- this is a big deal for me because I'm a bit crazy, but not for the rest of the human race, and I should look at it in those broader terms.

E-mail may be the way to go, if only to let me calm *down*. And, yeah, so neither of us have to scrabble for words. And no need to wait til I see him again, either ;)

(He does know I'm heading off for parts-3000-miles-away, but I'm still willing to try this, knowing that either it's on a timeline, or that I'll being trying to sustain one hell of a long-distance relationship. I kind of like the chaos of that; reminder that I don't know how everything ends up :) )

Also, hey, thank you all. I know relationshipfilter gets a bad rap, but you're all really helping me in something that seems really basic, but is also really important to me.
posted by kalimac at 9:31 AM on February 17, 2008

a follow up from the OP of this thread (regarding a similar issue):

"I rang him and asked if he wanted to go for a drink that weekend, and he said "yea, how about Saturday? I need to check my calendar, but I'll get back to you" and then he never got back to me, so I let it go and didn't bring it up when I saw him at the next group event. I feel that at least I did have a go, so I don't have that bitter 'wasted opportunity' feeling to live with, and hey, I'll never see him again so it's not like it's going to haunt me!"

Sent to me by a MeFriend (like my cute neologism? please no one ever use it again) with request to let this thread know a real life consequence!
posted by nax at 3:55 PM on February 17, 2008

"soo... when are you going to ask me out?"

Agreed that this is not the way to go; as someone who once got "why haven't you made a pass at me yet?" I can say that didn't set me up to have much respect for the girl.

That'd depend on the person & the circumstances. My real-life version was "sooo...are you going to take my number, or am I going to take yours?" which was about the cutest thing ever. I can only guess that the girl who made a pass at davejay wasn't one that he already fancied, or else he would probably have reacted with a "D'aw! How sweet!"
posted by UbuRoivas at 5:08 PM on February 17, 2008

Followup!

Got a reply to my e-mail today -- he gently turned me down, but it's due to shit he's going through himself, and he's not in a place to date anyone. So, not the ideal result (at least from my perspective) but at least it's finally *decided*. Also, you all rock.

(Also, I am happy to have it shown to me, very obviously and flatly, that this isn't as big a deal as I had thought it was. Everybody grows!)
posted by kalimac at 1:33 PM on February 19, 2008

well-done kalimac! People who take chances grow, people who don't, stagnate.
posted by kairab at 12:37 PM on March 2, 2008