Can I win over a dude through a grand gesture, or does that stuff just belong in the movies?
June 3, 2010 10:44 PM   Subscribe

Is it possible to woo someone? You know, like they do in the movies? I'm looking for creative suggestions on how to get back with someone I casually dated. Spoiler -- this is probably just a thought experiment. The likelihood I'll actually have the (figurative) balls to do anything is somewhat questionable. So let's be creative!

I dated a totally super cute sweet funny amazing dude for two months back at the beginning of the year and we split amicably for unfortunate-circumstances-related reasons. Busy-ness, job stuff, new relationship anxieties (on both our parts). Now, three months later I'm still pretty smitten with him and wondering what I can do about it. I've seen him around and had (very) friendly conversations with him that have always ended in extended hug sequences, but it's seemed too awkward and scary to make any sort of second-chancey type move.

Me -- mid-twenties, lady. I like to think of myself as sort of a catch --- pretty, smart, funny, somewhat nerdy, very well-liked. Not crazy. I repeat, not crazy. I think. i don't usually go in for the romancey-type mushy stuff, in fact am pretty pragmatic and blunt most of the time. a bit jokey and tongue-in-cheek -- my delivery is pretty good -- i think i could bring him flowers or something whilst seeming sincere yet playful and not overly creepy (uh, though it occurs to me that all creeps have at one point said something to that effect). he has a *great* sense of humor so something outlandish might get his attention. let's say box of chocolates on the bottom of the scale, tap dancing gorilla-gram is the ceiling here.

I understand no strangers from the internet can intuit the intricacies of the situation (and I myself can't read his mind, of course) but I'm just sort of wondering --- does this stuff even work? Can I 'Say Anything' him or are romantic gestures like that completely out of date? Were they ever realistic? And what are some cutesy, fun ways to let him know that I'm still very much into him, but also that I am not an obsessive crackpot? (you'll just have to take my word on that last one).

Thanks, strangers!
posted by custard heart to Human Relations (36 answers total) 13 users marked this as a favorite
Not to be too reductive, but have you tried the basics, like hanging out a lot, getting a bit tipsy, snuggling, things like that? Before you break out the big guns of flowers and tattoos of his name, maybe just invite him on a simple date?

I can think of lots of situations where wooing has worked -- but only when it stays this side of creepy, and the recipient was at least a tiny bit welcoming. And I can think of a lot more situations where people have gotten caught up in Grand Gestures and neglected the basics (like, say, holding hands in the rain and then kissing); blaming the failure on inadequately grand gestures kind of misses the point.

tl;dr: go for it and make your move, but don't overthink the process and forget to ask him out.
posted by Forktine at 10:52 PM on June 3, 2010

I like you already!

My best advice is music. Music music music. Burn CD's and mail them to him. Or don't, if street addresses are too stalker-ish. Leave them where he'll get them. Send him playlists. Play him a song outside his window at bedtime. Pop up in the backseat of his car and sing something. Ride on the hood of his car with a banjo and some apropos lyrics (heh, I'm being ironic now, but you know what I mean).

What songs does he love? What songs would he love if he only knew them? What songs say "custard heart + super cute sweet funny amazing dude?" get those songs to him!
posted by deep thought sunstar at 10:53 PM on June 3, 2010 [2 favorites]

What makes you think such an extreme is necessary? It sounds like you are on fairly good terms- can't you just ask him if he wants to get back together?

are romantic gestures like that completely out of date? Were they ever realistic?
I suppose someone at some point in history has successfully done something like that, although no one I've ever met. But usually it's to apologize for some major wrong, or win someone who has always been out of reach.
posted by drjimmy11 at 10:54 PM on June 3, 2010 [2 favorites]


unfortunate-circumstances-related reasons

Have these reasons changed? If not, don't bother. If so, just go out of your way to talk to him, and say "hey, remember those unfortunate-circumstances-related reasons we split up? I was just thinking about it, and you, and realized those reasons are no longer in the way. Any interest in going out for [whatever], or did we actually break up for other reasons that you didn't admit to me?"

Is that wooing? Nah. But if he's interested, you'll go out for [whatever], and if not, you'll find out so you can avoid wasting your time trying to woo him.
posted by davejay at 11:09 PM on June 3, 2010 [2 favorites]

Oh, and by the way, wooing is still an active part of our daily lives, right? We just don't call it that. We call it romance. Like the time a new girlfriend prospect asked me to pick her up a sandwich on the way over, and instead I picked up the fixings and made her a sandwich when I got there. Or when I met a girl at a bar, she dropped me off at another bar on her way to another thing, then when I got home a few hours later I called her and said "sorry for waking you but I would like nothing better than to have a 2am milkshake with you at the Golden Nugget" and she said "i'll meet you there in fifteen minutes."

If back in the day it was supposed to be flowers and chocolate and serenades, nowadays it's just exposing your vulnerability, taking a risk, and showing a little extra care in how we treat each other. I bet you can already think of a few him-specific things you can do.
posted by davejay at 11:15 PM on June 3, 2010 [21 favorites]

and just in case the Golden Nugget girl is reading this, yes, I know our relationship ended badly, but I still remember the way it started quite fondly. and the made-her-a-sandwich girl? she's my wife.
posted by davejay at 11:17 PM on June 3, 2010 [10 favorites]

Grand gestures are very, very tricky. If the intended target is head over heels for the gesture-er, then it'll go over really well and he'll be thrilled. If there is any doubt or lukewarmness about the gesture-er at all, it's likely to be kind of creepy and weird. And if he's head over heels in the first place? You don't need a grand gesture. Just be direct and talk to him. It seems like nobody does that anymore. Being honest and saying, "Hey, I like you!" seems so rare these days that it's a grand gesture unto itself.

On preview, I agree with davejay, it helps if you do something minorly unexpected or just a nice gesture. Relationships aren't about grand gestures, it's about the little ones that add up for one special person.
posted by Fuego at 11:31 PM on June 3, 2010

You might enjoy this question: Do romantic comedy gestures work in real life?
posted by LobsterMitten at 11:52 PM on June 3, 2010

The trick is to have one date, then if it goes well, do the weird romantic-ish thing.

You don't want to do something like that if he's not that into you, but you might as well do it because it sounds fun and entertaining and will charm him. Charming him is good.
posted by internet fraud detective squad, station number 9 at 11:58 PM on June 3, 2010

*but you might as well do it even if he is already into you, instead of as a way to win him over
posted by internet fraud detective squad, station number 9 at 11:59 PM on June 3, 2010

My $0.02: There's a fine line between proactive wooing and harassment, which the movies conveniently overlook.
posted by MuffinMan at 12:42 AM on June 4, 2010 [2 favorites]

I have a friend who, whenever he is at all interested in someone, asks them out on a date, looks them in the eye and tells them how he really likes them, and wants to know if there could ever be a romantic relationship between them.

He likes doing it, I suspect, because it takes the guessing and the worrying out of those first few encounters. It even sounds nice to rational people--but it's actually suicide, because he forces the moment too early, and people don't like to be put on the spot so they get flustered and say thanksbutno.

Point being: it might sound cute to woo on a big scale, but make sure you're not just doing it to protect yourself from a more conventional, sometimes uncomfortable "wooing period" of the sort that davejay describes.

On a related note, I tend to think some men hide behind grandiose gestures to mask insecurity. You said yourself that you're a catch! What's keeping you from asking him out for dinner or dessert or a fun date that shows your personality?
posted by ista at 1:03 AM on June 4, 2010 [1 favorite]

A grand gesture would be perfect if he was in doubt about your affection for him:

"I'm not sure if she really likes me or not..."

You land on his roof in a hot air balloon, play him a corny love song cover on the ukulele, then pick him up and fly to a secret picnic spot in the hills.

Now he knows you like him.

With your situation, however, it seems like the reason for the split wasn't that you didn't like each other, but that it just wasn't a good time for either of you. In that case, a grand gesture would seem (to me) a bit out of place. I'd say just let him know that your situation has changed and that you're still keen. Save the grand gesture for now.
posted by twirlypen at 1:52 AM on June 4, 2010

I've done the grand-gesture mixtape/CD sent anonymously with just my phone number on it; the songs were all clues to my identity. It got his attention, but that's all it got.

MeFi Hive is right about something: there has to be interest on his part as well, otherwise instead of ringing a bell you just get a >thunk<.
posted by kidelo at 3:11 AM on June 4, 2010

Can I 'Say Anything' him or are romantic gestures like that completely out of date?

They aren't, but if you watch those types of movies, the basics had already been covered. Starting with a huge romantic gesture before, like, telling them you like them seems a little weird, to be honest.
posted by Hiker at 3:22 AM on June 4, 2010

Maybe I'm completely sexist, but even when "grand gestures" might work, it's usually directed towards a woman. Seems like men are less likely to find these gestures compelling. Maybe they don't find them off-putting, but I can't imagine them actively attracting the men I know.

I've never seen those kinds of gestures work for my lady friends; it usually backfires as pathetic. If he's a straight-forward kind of guy and you're a straight-forward kind of lady, then be straight forward. I think you may be trying to hedge your efforts so you're not rejected directly, so it's worth cushioning it with a mix CD or something small, but don't spend much time or money on this effort.
posted by parkerjackson at 5:33 AM on June 4, 2010

Cookies & muffins. (or similar easily created and transported food items) Make them and give them to him.
posted by hworth at 5:55 AM on June 4, 2010 [2 favorites]

My ex-ex and I split because she moved to a different city for study, and I didn't deal well with the distance. That was in in early 2006.

Fast forward to early 2010. We met in another city, after she called me in December 2009, to say hi.

I still had old feelings for her, and thought "what the heck". So I kissed her, and now we're back together and happier than before. She'd had similar thoughts but was unsure of how to make a move.

The point is, make a move and make it big. Guys don't get "subtle". (Neither do a lot of women, for that matter).

Figure out what it is you WANT. What do you WANT? Why do you even want to woo him? Just kiss him, and see what happens. If it's on its on, if it's not it's not. And then you'll both be in a better place.

I say this from the experience of having once given a lot to a person, and she just took and took and took and hooked up with someone else.
posted by flutable at 6:03 AM on June 4, 2010 [1 favorite]

Most men love getting flowers at work. Or, in the alternative, cookie bouquets. But men so rarely get flowers, most of them *really* appreciate the gesture and love the attention they get from everyone else in the office.

I don't know if you'd be better off just asking him out, or if maybe it'd be easier to ask him out on the card of a floral delivery, or what, but if you decide to go "romantic gesture," I vote flowers, sent to the office.
posted by Eyebrows McGee at 6:43 AM on June 4, 2010

As a man, I would probably miss any subtle gesture and be confused by any not-so-subtle, but not explicit gesture. And not confused in a deep emotional way -- confused like "What's happening?"

If you're not gonna anonymously send him a banjo, take the simple direct 'hey do you want to go on a date?' route.
posted by wrok at 6:51 AM on June 4, 2010

I think grand gestures only work when the sticking point is the other person not accepting or believing that you are truly crazy for them. The grand gesture says to them, "Look. See me doing this ridiculous thing for you? Is that not proof enough that you've compromised my sanity? I love you."

If you liking him has already been established, then that's when it crosses the creepy line.

I did dress up as John Cusack's character from Say Anything (complete with boombox) for a Halloween party that my recent ex was attending. I'm not sure anyone got it.
posted by the jam at 6:51 AM on June 4, 2010

Speaking as a dude (in a bathrobe, with a rug that really brings the room together), a grand gesture would be nice, but you'd probably have just as good luck simply asking if things might work now.
posted by DaveP at 6:55 AM on June 4, 2010 [3 favorites]

For him to think you are an obsessive crackpot, he needs to be not at all into you. Extended hug sequences are sufficient evidence that this is not the case. At the worst he is going to say, "sorry but I still don't think this is going to work out." There's a good chance he is worried about the same thing you are.

Flutable is right, don't do subtle. Signals don't work well (especially with guys) because there is too complex a web of intent and cause and effect and you just get lost in your plate of beans.

Have there ever been an askme relationship question where both parties were asking about the other? ("OMG I am really into this girl but..." "OMG I just met this guy...") How long before this happens, do you think?
posted by ropeladder at 7:26 AM on June 4, 2010

Response by poster: Thanks! I chose Say Anything as a great example because at the point of the boombox thing (am i correct?) Ione Skye had broken up with Lloyd Dobler because she got freaked out or something, and he wanted to prove that he wasn't going to break her heart.

I sort of suspect the unfortunate circumstances had a lot to do with him getting spooked, as he is maybe a bit of a schlub and I know doesn't have the highest self-esteem, though I think he might also be the cutest, best thing i've ever laid my eyes on. I think he likes me, but would say no if just asked out. I need something that would catch him off guard.

I basically feel this way about him.
posted by custard heart at 8:21 AM on June 4, 2010

I don't think you need grand gestures so much as gestures, but from what I have learned (and others have echoed), guys don't understand subtle. You could buy him books he likes and send him expensive imported magazines from the UK with his favorite indie artist on the cover and a tiny painting from a homeless artist who he's always mentioned he liked - but to a lot of guys, those gestures will not automatically add up to I LIKE YOU AND LETS DO IT.

Smooching. Smooching him will get your point across. And you can still shower him with gifts if you want but I would just go with the romantic smooching.
posted by micawber at 8:29 AM on June 4, 2010 [1 favorite]

You know this person. You know what they like. Ask him out. Say "I have tickets to an improv comedy show - want to come with?" Another idea is to invite him over for dinner and go all out.
posted by xammerboy at 9:03 AM on June 4, 2010

Go get a 6 pack of decent beer and then go to his place as a surprise. If he's free, hang out n ask him out again, if he's busy leave the beer and let him know you were just thinking of him then the next time you talk ask him out.
posted by WeekendJen at 9:35 AM on June 4, 2010

I am cautiously anti female-to-male gestures because the men in my life have always responded better when I have made them suffer challenged them a little than when I have lavished them with gifts and adulation which they must passively receive.

Why not spike the ball hard into his court and see if he rises to the challenge? "Take me to bed or lose me forever" might be a little drastic, but "When are you going to kiss me?", (delivered with an imperious look) recently worked for a friend of mine.
posted by stuck on an island at 9:39 AM on June 4, 2010 [1 favorite]

As you said, no one reading your text on the internet can fully know you or his situation. I'm gonna say you don't sound crazy, but here's a creepcheck for you to evaluate yourself.

Do you view this guy as an idea, not a person? Do you recognize that this person has free will, right to opinions (including not liking you), personality, flaws etc? Are you dreaming up a fantasy where this person is a character not a human?

If you've passed the creep test, then you've got the green light for any gesture mentioned above.
posted by fontophilic at 10:19 AM on June 4, 2010 [2 favorites]

Oh, and lest that seem heartless or manipulative, I should add that it only applies to the period of uncertainty before you become an item. Once past the smooch barrier, by all means let fly with the mixtapes and home baking!

I wish you luck. You sound like an awesome, fun couple in the making.
posted by stuck on an island at 10:20 AM on June 4, 2010

A girl back in college once got me to go out with her by leaving a trail of M&Ms from my front door, down my stairs, across the parking lot, three blocks away, into a bar, and right up to her table, where she was waiting with a pitcher of beer for me and my roommate.
posted by ColdChef at 10:20 AM on June 4, 2010 [6 favorites]

You know what you need to do. You need to write a really fantastic, dad-joke filled stand-up routine, creep around his local watering hole (you know the one), get enough liquid courage into you, stand on a table, and deliver it to him. No creepy neck kissing in the neighbour's doorway, you already know that doesn't work (so I'm calling for an immediate recall of all smooching suggestions, unless the smooches occur above the chin, and chin doesn't count as above the chin, understand?)

But I also think you should send him a banjo.

And also? Fuck him if he doesn't come around. You are eleventy times more awesome than he is (but sure, he's pretty and funny-ish) and I really think you should consider WHY you want him so much. Is this because he won't let you have him or because you really like him? Figure that out before you waste your time, sweetie, because it'll be a sad mess if you don't.

(But yes, this is a situation where a grand gesture might work. Or at the very least, be well appreciated.)
posted by Felicity Rilke at 10:55 AM on June 4, 2010 [1 favorite]

Response by poster: !!!
That's taking this so very literally! I'm just looking for cute ideas about how to charm someone. Can you think of anything else more fun to spend your time thinking about?

PS LOVE the M&Ms!
posted by custard heart at 12:22 PM on June 4, 2010

Building on the M&M's idea, how about a treasure hunt? Stash treats (little poems, silly drawings, plastic toys, candy) in different locations and accompany them with a clue about the whereabouts of the next clue. The last clue can lead to you, and a pitcher of beer, or whatever you think he'd enjoy.
posted by millions of peaches at 1:50 PM on June 4, 2010

With guys I find that you need to be fairly direct, but it helps if you arrange it so that it feels to them like it was their idea. Basically, go out for drinks, and then talk about sex.
posted by 5_13_23_42_69_666 at 2:05 PM on June 4, 2010 [1 favorite]

A girl back in college once got me to go out with her by leaving a trail of M&Ms from my front door...

Heh. A girl back in high school got me to go out with her by claiming she was kicked out of her dressing room by the other girls, asking if she could change in ours, then (when I was the last one out of the room to let her change) grabbing me and kissing me.
posted by davejay at 3:29 PM on June 4, 2010

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