I feel like a boy crazy middle schooler all over again
February 8, 2012 9:27 AM   Subscribe

I recently reconnected with a guy that I hadn't seen in ten years. (We were fourteen then, and we're twenty-four now). After getting some friendly drinks, I'm interested in pursuing things further.

I recently met up with someone from an after school activity back in middle school that I hadn't seen since, uh, middle school. I went to this meeting up for drinks with a feeling of dread, maybe expecting to make a new friend but mostly dreading the potential awkwardness, and I was pleasantly surprised. And now I can't stop thinking about him. Ugh!

In other words: I had a crush on him when I was thirteen. It's rearing it's ugly (?) head again.

I was getting definite signals that he was at least flirting with me, and he mentioned that he was going to be really busy for the next few weeks, but that we should get together after his life calms down. (Legitimate work/apartment issues - I just want to leave out some detail). I'm wondering how I can help move that process forward, and not cockblock myself into another friend-zone situation.

A little background: I'm very attractive, but I'm a little rough around the edges and I've always been "one of the guys."

posted by ablazingsaddle to Human Relations (26 answers total) 1 user marked this as a favorite
"Hey--it was really fun seeing you again the other night. Do you wanna come get a drink with me on Thursday?"
posted by Admiral Haddock at 9:32 AM on February 8, 2012 [2 favorites]

So . . . you ask him out after a few weeks? I mean, I know it's scary/exciting, but there isn't really any conflict here, is there?

Posting this question to askme is just begging for us to read too much into the "busy for the next few weeks" thing. Unless there's more context, just be confident and buy him a drink.
posted by Think_Long at 9:33 AM on February 8, 2012 [8 favorites]

A slight variation on Admiral Haddock's answer that leaves the timeline a little more open-ended, like "Hey, when things calm down for you, would you be interested in getting a drink some time? Let me know what works for you."
posted by futureisunwritten at 9:36 AM on February 8, 2012 [4 favorites]

he mentioned that he was going to be really busy for the next few weeks, but that we should get together after his life calms down

If the issues are indeed legitimate and he gave you a timetable then I think you're in good shape. You were hanging out and he was already thinking about the next time you'd be hanging out.

You know what, just call the guy. Tell him something like: "Hey, I had a really awesome time and I know you're gonna be busy for a while and I agree that we should get together after. So I was thinking, right...whenever that turns out to be, would you be all right with maybe calling it a date?"

The worst that can happen is he says no.

Let us know how it went, yeah? I like happy endings and I like your chances.
posted by FAMOUS MONSTER at 9:38 AM on February 8, 2012

Explicitly state that you want to go on a date. Not get drinks, not hang out, but a date.

Something like this: "Hey, when you're down with the work/apartment issues, I'd love to go on a date with you."

You want to make your intentions crystal clear.
posted by Brandon Blatcher at 9:39 AM on February 8, 2012 [4 favorites]

I agree with FAMOUS MONSTER and Brandon Blatcher. Ask him to go on a date once he gets some free time.
posted by Brian Puccio at 9:53 AM on February 8, 2012 [1 favorite]

"Hey that was fun, when do you want to go on a real date?
posted by 2bucksplus at 9:53 AM on February 8, 2012 [1 favorite]

I hate to threadsit, but I like the idea of suggesting a date without using the word "date," because no one uses the word "date." Not unless they're "dating." I figure if I show up looking nice, and I don't say "Let's hang out!" I should be fine, right?
posted by ablazingsaddle at 10:05 AM on February 8, 2012

Wrong. "Let's hang out" says a lot of things - "I haven't decided how I feel" and "Enjoyed spending time with you but don't get any ideas" are two of them.

You want a date. Ask him out on a date.
posted by Lesser Shrew at 10:10 AM on February 8, 2012 [11 favorites]

No. You want to telegraph your intentions before you go out. You want to let him know what you want before ya'll go out, so he can say "HELL YEAH" or "uh, let's just be friends"

Yeah, it's entirely possible he's on the same page as you and interested, but you want to be clear, especially if you're usually one of the guys.

If you really don't want to go that route, then get his number and send him a few flirty texts while he's busy those weeks.
posted by Brandon Blatcher at 10:12 AM on February 8, 2012 [4 favorites]

Everyone uses the word 'date'.
posted by MangyCarface at 10:18 AM on February 8, 2012 [4 favorites]

A little background: I'm very attractive, but I'm a little rough around the edges and I've always been "one of the guys."

That's three positives right there. Remember that it has been the same time, and the same ages for the guy. He must be thinking about it too. Taking the initiative and asking him out on a Date would put the awe in awesome.
posted by CautionToTheWind at 10:49 AM on February 8, 2012

I get the problem with the word 'date'. Try saying things like:

- I would love to see you again / it would be great to see you again
- I've been thinking about you a lot since I last saw you
- I have to say, I can't believe how handsome you are as a grown-up / you are just as cute as I remember / even more cute than I remember / etc (add smiley faces to indicate that you are blushing a bit while you say this)
- I am glad you popped back into my life

In other words, flirt a bit and say some simple things that are slightly beyond the boundary of friends negotiating a hangout.
posted by PercussivePaul at 10:50 AM on February 8, 2012 [6 favorites]

Everyone uses the word date. Don't set yourself up for friend zone or mixed messages.
posted by These Birds of a Feather at 10:51 AM on February 8, 2012 [1 favorite]

Percussive Paul gets where I'm coming from.

I understand the problem with "Let's hang out!" and I was not planning on saying that, but I would like a little gray area and something flirtatious enough to not get friend-zoned is as much as I think I can pull off in this situation.
posted by ablazingsaddle at 11:54 AM on February 8, 2012

Dear X,
I really enjoyed getting together [comment on middle school? comment on that meetup?]. We should do it again sometime.
I hope everything goes well, good luck with [issue]. I know you said it'll be a few weeks, so I won't pester you until you're done - but I do like the idea of meeting up when you can, whether that's for a real date, or just to grab a friendly coffee.
Talk to you later,

He'll get back to you. You've dropped the word "date", which invites him to mention any extenuating circumstances (the girlfriend, the broken heart, the excuse, the no spark), or to explicitly say "yes, a date!". Worst case scenario, he is deliberately vague in reply, but at least you'll know that's not your fault.
posted by aimedwander at 12:04 PM on February 8, 2012 [1 favorite]

"he mentioned that he was going to be really busy for the next few weeks, but that we should get together after his life calms down."

I think you should wait a couple of weeks, since he said he was going to be busy, and then get in touch if he hasn't contacted you. Ask him how his stuff went. Then just ask him if he wants to get a drink, if you really want to. That's a way to avoid using the word, "date" and it implies a level of adult intimacy. I personally would not appear too eager, since he said he wanted to get together later rather than sooner. Keep your head on your shoulders and take the long view.
posted by amodelcitizen at 12:20 PM on February 8, 2012

I wouldn't say anything like "I've been thinking about you" at this point. Too mushy and you don't know where his interest is.
posted by amodelcitizen at 12:24 PM on February 8, 2012 [1 favorite]

eh, there's nothing to be gained by caution, so what if we don't know where his interest is. If they play it too friendly, they'll wind up friends. If he likes her then he likes her, if he doesn't then he says no or doesn't reply, the only risk is coming on too strong and scaring him away if he is hovering on the boundary of romantic interest, where a subtler touch -- planting the idea and then stepping back -- might have brought him around. I agree there is an art to this and one has to use a light touch and not go overboard with the mush; just think of one thing that a crush would say and an old friend wouldn't, I think.

To me the word 'date' has a concreteness and a finality to it, in that it demands a yes or no, and actually imposes on the other party by putting them on the spot when they may not be ready. It calls the question, maybe before the answer is known. Plus, the event itself will come with 'date' baggage and 'date' expectations and maybe even 'date' anxiety once you've described it with that word. Not everyone uses this word. I used it once and almost scared away a girl who became a girlfriend. She hesitated for a few heartstopping seconds before saying 'sure' even though I was certain there was something there. She later told me she felt put on the spot and almost said no as a reflex, even though she was totally crushing on me, just because, well, if you're not sure what to say, you say no. These things are complicated; we all know this.
posted by PercussivePaul at 12:46 PM on February 8, 2012 [1 favorite]

Yeah, I don't know, I'm 28 and only recently started using the word 'date.' Nobody I knew did before the age of 25, really. It can definitely sound weird, I'm still trying to get used to it.

Anyway, though, I can say from experience that it is totally fun to hook up with a guy you had a crush on in middle school/ high school, many years later. I highly recommend it. Just invite him out for a drink and after you've both had a couple and you're flirting, you can tell him "So . . . I totally had a thing for you in middle school." Chances are the response to this will be positive and then you can just go for it and make out with him. If that goes well, then you can suggest hanging out again sometime soon. Don't sleep with him right away, part of the magic of situations like this is the feeling of both being young and innocent! Enjoy that feeling for a while.

He's married now, but I have to say one of the most fun things I did in college was the above (drinks followed by making out) with the homecoming king from my high school. I'd had a crush on him since the very first day I met him freshman year . . . with his dorky braces and all, sigh . . . Anyway, when we reconnected in college I realized pretty much immediately that we were way too different to actually date, but there was something so satisfying about living out my little high school dream for one night. I'd approach it that way- keep it casual. Enjoy the moment, don't plan too hard for the future, and don't assume you know that much about him yet or that you're super compatible or anything. But do get drinks. Taking that young, giddy, unrequited-crush feeling of adolescence and adultifying it with an alcohol buzz is so much fun it should be illegal.
posted by GastrocNemesis at 1:01 PM on February 8, 2012 [1 favorite]

MeFites are absolutely terrified that a romantic situation could ever get the least bit romantic. Stamping out any kind of ambiguity is the best way to do this. Ambiguity equals manipulation equals drama equals pure evil. Well, I am going to be the outlier here.

The word "date" stamps out any kind of ambiguity. If you had written to us to say that you had been carrying a torch for this guy for eight years, spending every waking moment with him, giving him puppydog eyes, and you've been desperately in love with him for every second of those eight years, I'd say to use the word "date". In a situation like that, ambiguity is not your friend.

If you had been hanging about on the fringes, seeing him during group activities, carefully placing yourself only a table or two away, and casually mentioning the vague possibility of possibly ending up in a group that may eventually appear at a large event at roughly the same time that his big group might eventually appear at that same event, and you were under the impression that by doing this you were asking him out on a date, I'd say to use the word "date". In a situation like that, ambiguity is not your friend.

So, how to initiate the delicate dance of ambiguity without becoming a manipulative drama-monger of pure evil? Okay here's what you do. Do not volunteer to go over to his house and clean out the grease trap. Do not organize an outing for your Glee Club and his Glee Club to attend a rugby game together. Do not, in short, arrange to do oafishly unromantic things with him in oafishly unromantic situations.

Also do not bug him and get all up in his grille and call him tonight and say "hey dude hey hey dude when can we go out? are you done being busy yet?" and then have a long self-revelatory conversation about your childhood issues and your stepmother's rejection of the parakeet and its effect on your lifelong bedwetting problem. Nor do you follow that up by calling him another 22 times.

Instead: radio silence. Then, in two weeks' time, if you haven't heard from him, you send him an email like: "Hello there. It was an absolute delight to see you again. I'm sitting here on my cherry-blossom covered porch, drinking the lemon and ginger cooler I made this afternoon [or whatever: don't say you're sitting there in your ratty dressing gown covered in soup, having spent the afternoon cleaning out the grease trap; be romantic], and my thoughts drifted to our conversation and the things you said about [romantic-compatible yet just ambiguous enough topic]. I do hope we will see each other again soon. Yours, ablazingsaddle xoxo"

Then, do nothing further. If he wants you, he knows where to find you. Fragrant, cherry-blossom [or whatever] you.
posted by tel3path at 1:23 PM on February 8, 2012 [9 favorites]

Thanks for the variety of thoughtful answers, guys!

I agree that the word "date" is too serious, too concrete, and puts some sort of pressure on the situation. I will use a light touch, I won't force the issue, but I won't bro-dude all over the place/talk about other guys I'm fucking/bring a six-pack to his apartment looking like a total scrub.

Some information that I should have - and thought I did, but I'm dumb - included in the original question: It has been about two weeks already, so I feel like I have to act now. We have mostly been communicating via text. I'll text him in a bit, keep it mildly flirty, and see where it goes.
posted by ablazingsaddle at 2:15 PM on February 8, 2012 [1 favorite]

I might be a little late to the party on this one, but just in case...I think the phrase 'get together' works well in situations like this. For some reason, twentysomethings almost never use the word 'date,' so I see your reluctance there. 'Hang out,' however, sounds too friend-y, you hang out with your buddies.

So say 'get together,' suggest a date-y activity, and be specific about it: 'Hey, you want to get together for dinner sometime soon - maybe Saturday?' Something like that.

Also, I generally prefer email or phone to texting in these kinds of situations, but if you've already been texting, I'd guess it's OK.
posted by breakin' the law at 4:14 PM on February 8, 2012

I'd tell him I really enjoyed catching up and would like to go out again once his schedule clears up, or if he just needs a night out.
posted by myShanon at 5:55 PM on February 8, 2012

The reason I agree with Blatcher and others that the word "date" might be a good idea is that you sound, well, kind of awkward about this. You describe yourself as a tomboy who doesn't have much dating experience, and frankly, you don't have a question here other than how to take things further when he has already told you he wants to hang out when his life settles down.

I think there are a lot of good ways to play this and I like tel3path's suggestion; my only concern is that if you don't know how to do this (and you don't, which is why you are asking this question), the way that will work best for you is to be straightforward. I mean, yeah, you could say "when are we going out again" instead of "we should go on a date," but that's still straightforward and does not leave the "gray area" that you seem to be looking for.
posted by J. Wilson at 6:15 PM on February 8, 2012 [1 favorite]

Don't say "date" if you think it feels weird. Say "dinner." Invite the man out to dinner somewhere date-ish. Say, "It was great to see you last week. I was wondering if you'd like to get dinner one night at XYZ." He'll look the place up if he doesn't already know it, and he'll know that it's a date.

Wear lipstick and come prepared to pay the entire bill, because you did the asking. Have fun!
posted by elizeh at 7:39 PM on February 8, 2012 [1 favorite]

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