Say Anything!
February 19, 2010 9:12 AM   Subscribe

Have you ever performed a romantic-comedy-type grand gesture to win over a woman in real-life? If so, what was it and what were you thinking as you were planning/executing?

I'm writing a work of fiction (not totally sure yet whether it's a novel or a play), and I'm creating a male character who is trying to win the heart of a female character by doing all of the cheesy stuff that people do in romantic comedies. Serenading on her front lawn, sending a hundred roses to her office, writing long love letters about his passion for her, anonymously sending her a banjo, etc.

I'm having trouble getting inside this guy's head, plus I'd like some ideas for moves that are a little more realistic, less cliche. So I'm looking for people who have, in real life, performed big romantic gestures for someone they were trying to woo. I'm interested in both plans that worked and those that didn't.

I'm interested in what you did, but I'm also interested in what your thought process was. What were you thinking and feeling as you planned it? Did you have a specific vision of how it would go and how she would see you? How were you hoping she'd react? Did you tell your friends what you were planning to do, and what was their response? What was her response to the event? If it didn't work, how did you feel afterward? Did you try something else? Have you ever done something like that a second time?
posted by decathecting to Human Relations (33 answers total) 26 users marked this as a favorite
I serenaded her outside the window of her heritage apartment. At dusk. In spring. With the cherry blossoms falling all around. Singing, oddly, "Electrolite" by REM. With my friend on stand-up bass. That's pretty much a total cliche, but it worked pretty well. Plus her roommate was madly jealous.
posted by dbarefoot at 9:16 AM on February 19, 2010 [1 favorite]

Yep, previously. (first-year anniversary was yesterday! wohoo!)
posted by tmcw at 9:21 AM on February 19, 2010 [1 favorite]

This wasn't me, but this happened TO me.

My boyfriend (at the time), who was without car because it was in the shop, walked thirty miles from his house to my place of work, when I was working somewhere that I really couldn't be interrupted in the middle of the day, or just take off on a picnic, like he'd planned. He was pretty upset that I was mad at him for walking thirty miles to surprise me.
posted by roomthreeseventeen at 9:25 AM on February 19, 2010 [1 favorite]

Response by poster: I saw that other question, which is about being on the receiving end. I'm specifically interested in the givers, and in what they're thinking. So if you've been a recipient and can get the person who performed the act to chime in, that would be great. But I'm really mostly interested in the people doing the awesome stunts. And I'd love to have more information about the specific thought and planning process for this sort of thing, which recipients can't really speak to.

(and yes, the banjo thing was a joke reference to that other question. But it's a legit example of the sort of thing I'm looking for, and that guy's question and responses were really helpful in my thinking, so I'd love more of that sort of thing.)
posted by decathecting at 9:33 AM on February 19, 2010

When I think big bold rom-com gestures, I think Jumbotron.
posted by contessa at 9:33 AM on February 19, 2010 [2 favorites]

I participated in an over-the-top gesture.

My college roommate was about eight hours from home and her high school boyfriend. For her birthday, he asked me to help him pull off a heist--a friend and I started planting notes in our mailbox like ransom notes, with the letters cut out of magazines. It escalated into her getting blindfolded and us riding around supposedly being directed by some mysterious person on the phone, until we wound up at a fancy Italian restaurant downtown where her boyfriend was waiting with a dozen roses to take her to dinner. She thought he couldn't get off work to come see her, so she wasn't expecting to see him at all.

Now, in this situation, this was a guy who already had the girl, so to speak, but I know he wanted to do something that she would be talking about forever. I don't even think their eventual engagement topped this! Aside from just showing him how much he loved her, he knew that she really loved surprises (giving and receiving) and wanted to make that come true for her.
posted by peanut_mcgillicuty at 9:44 AM on February 19, 2010

Mod note: A few comments removed. In-jokes aren't answers, folks.
posted by cortex (staff) at 9:45 AM on February 19, 2010

When I'm planning a surprise romatic gesture for my husband, it's a lot of fun. I'm not exactly imagining the conversation or the scene or his reaction, I'm just idly daydreaming about him being happy and about how happy things like that make me. I don't really go for the classic "declare my love to the world" displays, more just doing unexpected favors, or bringing along a surprise augmentation to a planned event. (we're back at out cheap yukky hotel after a long day of dealing with family, and I pull the "oh, I think I left a box in the car, could you go get it?" move, and when he comes back with it, I set it down, and pull out wine (winter-chilled), glasses, chocolate, cheese, and a DVD).
It's like going Christmas shopping, or - for the crafty type - spending hours making a present for someone. I don't imagine the person saying anything in particular to thank me for knitting them a scarf, but I have a lovely mental image of that person being happy and good-looking and wearing things that match the things in my hands. Just daydreaming happy thoughts. When I was recently doing a bunch of cleaning and home-maintenance tasks while my husband was out of town, I was imagining him walking in the door tired of travel, worn out from his job, and dreading the transition to the new list of things to do (unpacking, cleaning out the car, finding dinner, remembering that the washing machine is broken, etc) but then being presented with a clean living room, uncluttered office, an utter lack of household to-do lists - it was great to just imagine the sense of surprise and relief, and I knew he'd get the message that I love him, and that I missed him, and that I was happy he was home even though I wouldn't see him till I got home from work. I suspect that's roughly how he felt; he thanked me profusely, but we didn't really talk about it.
posted by aimedwander at 10:02 AM on February 19, 2010 [5 favorites]

I was dating a guy long-distance during one of my college summers. One night, right around midnight (when I was expecting his phone call), I heard a noise outside. He was in the driveway, throwing pebbles up to get me to look out my second-story window.

He said that he'd driven half an hour for band practice and didn't have other things planned the next day, so he just drove another 2 hours north instead of half an hour back home :P
posted by Madamina at 10:23 AM on February 19, 2010 [1 favorite]

When I was 21, on Valentine's Day, I broke into my boyfriend's apartment...with a take-n-bake pizza, a case of beer, CDs, movies, etc. in tow. Discovering that his kitchen was a disaster (and unsuitable even for baking a pizza), I decided to clean the whole damn thing, including the oven of course. Next, I showered, got undressed, put on a sexy underwear set, and waited patiently in his bed, reading a book, until he got home from work.

Unfortunately, his roommate Joe came home and thought he heard something in the bedroom. Opens the door, where we proceeded to scare the living shit out of each other. We had a fun little awkward conversation, including him thanking me for cleaning the kitchen, and after which he let me know that he decided he felt like heading out to a bar and would very likely not be home until quite late.

There are many things about my plan I would have done differently.
posted by iamkimiam at 10:35 AM on February 19, 2010 [16 favorites]

To be clear, I took my clothes off before I got in the shower.
posted by iamkimiam at 10:36 AM on February 19, 2010 [7 favorites]

Best answer: I apologize. This is long.

I have done a number of things like this, but I'm a woman, and I was doing them for men, so, I'm not sure if I fit your criteria. I imagine, though, that the thoughts behind it aren't too different:

What were you thinking and feeling as you planned it?
     "I hope I can pull this off. Oh my god, what if I do pull this off?" I felt nervous, but in a deliriously intoxicating sort of way. I was full of adrenaline, for days sometimes, as I made my plans, and I felt like I would separate into millions of individual buzzing molecules if I achieved my goal (sometimes the goal was "get this person to fall in love with me"; others it was "get this person who already likes me to think I am the most amazing girl ever"). On all occasions, I was not suited for the people I was trying to woo; that was part of the impetus. I was trying to become the right girl through sheer force of will.

Did you have a specific vision of how it would go and how she would see you? How were you hoping she'd react?
     Of course. Each time I've made a grand gesture, during the course of its planning I have replayed, over and over in my mind, hundreds of possible positive outcomes, from general happiness and a Hollywood-style kiss, to eventual wedding bells. No matter how well it comes off, the reality of what happens never lives up to the possibility. It is always more fun to imagine what might happen than it is to live the actual consequences of the deed.

Did you tell your friends what you were planning to do, and what was their response?
     No. Mine have never needed other people's involvement. Part of the fun was keeping the secret. I've told friends after the fact, and the response is almost always some variation of "That takes chutzpah!" Often, it seems that such gestures are more appreciated by my friends than they are by their intended recipients.

What was her response to the event?
     Usually underwhelming, though positive. Invariably, the recipient doesn't understand the effort I went to to make the event happen. Most of the time, the recipient doesn't get the message I was trying to send through my gesture. I was using grand gestures in place of actual communication. I was too nervous and afraid of rejection to tell these men how much I liked them and wanted them, so I tried to show it instead.

If it didn't work, how did you feel afterward? Did you try something else? Have you ever done something like that a second time?
     I felt proud for having gone through with it, but disappointed that it didn't work (or, that it didn't work the way I had imagined it would). I never did a grand gesture twice for any one person. Eventually, I realized that, for me, the grand gesture was a replacement for communication. I stopped using them, and started talking instead. (I still struggle with being able to express my feelings that first time I tell someone I like them; it's incredibly hard to do.) And I found that saying "I like you. I like being with you," and hearing whatever response that prompted was far more satisfying than anything I'd ever gotten from grand gestures.

I still make small gestures of love; but I make sure that these happen after I've already communicated my affection for someone, and that person has reciprocated it. Once I've done that, it takes away my expectation of and need for a large response, and I can do these little deeds as true gifts, given without expecting, needing, or wanting something in return (or, at least, that expectation of a particular outcome is replaced by excitement over what the outcome might be).

For me, grand gestures were a phase that I grew out of; perhaps, if I find someone I'm in love with for the long haul, they'll return someday as a larger version of the small gestures I make now. But it seems to me that they were my attempt at a shortcut to love ("If I do this, he will love me") when there are no shortcuts to love. That's part of why they're so powerful in stories: that's the shortcut that everyone's looking for.
posted by ocherdraco at 10:42 AM on February 19, 2010 [21 favorites]

When I was in high school my boyfriend broke into my (mom's) house, left a trail of rose petals from the front door, down the stairs and to the back door, and was sitting in my back garden ready to serenade me with a guitar and a song he wrote.

Hilariously, the song very obviously was not written for me (it was written by him for his former crush, in fact), so I called him on it, asked him what he was thinking. He muttered something about how he figured I wouldn't notice would just be blown away by the romanticness of it all.

I asked him to clean up the rose petals.
posted by citywolf at 10:47 AM on February 19, 2010 [8 favorites]

Oh, that reminds me...same boyfriend, two months later, on my birthday brought me something like 12 dozen roses - seriously they were laid out in a fan three feet wide. Must've cost hundreds of dollars. Or he robbed a truck. Anyways, he looked like a red peacock with its body on backwards, coming through my (thankfully) double front doors. I wish I could tell you more, but I don't know what he was thinking.
posted by iamkimiam at 10:52 AM on February 19, 2010

Best answer: I actually did buy someone a banjo and posted about it in the banjo MeTa thread: (sorry no link, I'm posting from my phone). It landed with a thud pretty much, although the relationship has done well. In my case I was truly giddy in love and I didn't really have any ulterior motive to "win someone over" or anything like that. I suspect, as far as Grand Romantic Gestures go, this is uncommon. In most cases, I think they are acts of desperation performed by people who in some small part of their soul realize the target of their affection isn't that interested in them. If you want this to work as a plot device, the two people involved need to share in a lot more with each other than a single gesture before they fall in love and live happily ever after. At least that's the way I think it works in real life.
posted by Slarty Bartfast at 10:57 AM on February 19, 2010 [2 favorites]

I once considered making my girlfriend (who I had already been with for a few months, at the time) a buckyball from modular origami units. It would clearly have taken me a significant amount of time to complete, and I thought the symbolism of an object held together by a difficult to construct but ultimately stable symmetry was appropriate.
posted by phrontist at 10:58 AM on February 19, 2010 [2 favorites]

In most cases, I think they are acts of desperation performed by people who in some small part of their soul realize the target of their affection isn't that interested in them

Slarty has it. I don't think these really over the top things are indicative of a healthy view of the relationship.
posted by phrontist at 11:00 AM on February 19, 2010 [2 favorites]

A friend of mine did the following, which worked and which I would never, ever do no matter what: He dressed up in a full suit of armor, got on a horse with a lance and the whole kit, and rode up on her front lawn singing showtunes.

Yeah, I'm vicariously embarassed just telling you that someone other than me did that.
posted by The World Famous at 11:23 AM on February 19, 2010 [6 favorites]

Best answer: I have courted outlandishly and been courted outlandishly. sometimes at the same time. and I'm assuming that you're asking about courting, and not things that happen once you get to know each other and courting turns into being in a relationship.

when it is done well, it's an act of something like faith: there's the uncertainty of the situation and how much is at stake, and how it makes the risk you're taking unimaginable. (yes, unimaginable. like ocherdraco said, the kind of people who do these things are not so good at talking about their feelings.) it could go wrong, you've no reason to expect it not to, and it's terrifying and faith is the closest I can get to what it is that gets you to actually see it through.

done badly, however, there's something disgustingly narcissistic about it. how it becomes about building yourself up as clever and creative and romantic and almost bullying the target of your affections into a date. because she'd have to be a bitch to turn down someone as great as you. (or, on preview, what slarty said.)

I think the difference is in how honest you are, with yourself, about the risk involved.

in practical terms, when it is done badly all you expect of the person you're wooing is an acknowledgment of the great lengths you've gone to to please her-or-him. the kind of breathless giggling and clapping that's expected of the woman who plays the love interest in an Adam Sandler film. because there isn't really much more to the plan than that.

when it's done well, it works like an invitation to a game. when I first moved to England it took me forever to get a phone. (because sorting things like that out is sometimes beyond my ability.) so someone who had taken an interest in me dropped a letter through the mail slot of my door. for the next couple of weeks we exchanged these amazingly intense letters we delivered ourselves in the middle of the night. much better than having a phone, actually.

(or, in response to ocherdraco's realisation that her grand gestures were a replacement for communication -- grand gestures work best when they're a way of communicating.)
posted by spindle at 11:26 AM on February 19, 2010 [4 favorites]

Well, I pulled cash out of the bank and bought an airplane ticket at fantastic cost to come across the country to see her, just on a tiny suggestion that she'd like to see me, so that I could surprise her by being there all of a sudden the next day. I had this idea that I wanted her to just turn around and I'd be there; it wasn't exactly like that, but it was indeed quite romantic.

Guess it worked well enough. We got divorced last year. So there you are.
posted by koeselitz at 11:32 AM on February 19, 2010 [3 favorites]

Best answer: And what happens afterwards*? Because then you're just a 21st century guy wearing a bunch of armor, standing on a street sidewalk with a horse. Possibly needing to pee.

I think that these are the parts that they never address in the books, movies, etc. And I can tell you from personal experience (I've done a few extravagant things, but would rather not continue to overshare here), that there's always a period of wonderfully blinding awkwardness that inevitably ensues. When the music stops, every singer must find a way to gracefully get off his or her bad karaoke stage and rejoin the audience again.

But I'll say this, the common theme I think in every stupid gesture I've done has been one of seizing opportunity. When I have somebody to play with, especially in the beginning, there's a part of me that says, "Hey, I want to do all those silly things I daydream about. Maybe I can do that with this person. Maybe I can also make them really, really happy. As happy as I feel right now." That's what I'm thinking. I don't care about the outcome even. It's really selfish when you think about it. And a possibly unhealthy and unrealistic view of relationships.

Then again, if you've got something good going, you kinda don't want to get some foot-on-the-ground perspective. You're excited about somebody. You have energy. You don't care about being ridiculous. You're in love, or something like it.

*I mean, after you both ride off, of course. Because surely you must eventually come back?
posted by iamkimiam at 11:37 AM on February 19, 2010 [4 favorites]

I did a grand gesture for my parents - does that count? I flew home across country to surprise them. I did it because I wanted to see their faces when I showed up. They generally cry at the airport when I arrive; so I figured that if I surprised them they'd be even more happy.

I remember walking in the door with my sister who picked me up at the airport, giggling to ourselves for our cleverness. My parents glanced at us, glanced away, glanced back, did a double take, and started complaining that I hadn't even told them I was coming (they like the anticipation - now I tell them well in advance so that they get the maximum enjoyment of my trips).

So yeah, haven't done that again. I guess I've learned that stuff I think is grand in my mind is not so grand in real life. And that what I enjoy isn't what other people enjoy (although maybe it is - we both were enjoying the anticipation but when I surprised them, only I got to enjoy it). I've also had someone do that to me and it was horriblehorriblehorrible - and if I knew what he was thinking it would have saved me a lot of money, stress and therapy.
posted by hydrobatidae at 11:55 AM on February 19, 2010 [1 favorite]

Best answer: When I was 17 I was on a solo trip through Europe and met an English girl at the Munich train station. I didn't have a room, but I had a Eurailpass, so I was going to take a train to anyplace four hours away, sleep on the train, and come back in the morning, but when she said she was going to Paris I said I was going to Paris. We arrived in Paris at dawn having chastely slept together (I was way too shy to make a move), hung out for a couple of days, then parted ways. We'd exchanged addresses and after a couple of days I decided I was in love with her and had to go to England to see her. (Since the Eurailpass didn't cover England this meant additional expense that would blow my budget.) I took the channel ferry to England, took a train to Birmingham, took a bus to the town where she lived, walked up to her house, and knocked on the door. And her boyfriend opened the door.

Several years later I was on a trip with some buddies and I flirted with an Irish girl on the train from Dublin to Galway. I wasn't sure if flirting worked the same way in Ireland as it did in the States, so we parted ways in Galway. Many glasses of Guinness later I decided I was in love with her and had to go see her. I rented a bike and rode it about 15 miles down the Irish coast. Since the furthest I'd ridden a bike before was about a mile, I got really sore after a while and was basically pushing the bike up one side of a hill and coasting down the other. I met up with her at her romantic job playing a harp at a Renaissance-themed restaurant. I walked her home after her show, carrying her harp in the beautiful moonlight, we got to her place, and her boyfriend opened the door.

0-2, baby!
posted by kirkaracha at 12:28 PM on February 19, 2010 [22 favorites]

Why not send a memail to this guy? I'm guessing his grand gestures didn't just start after they were married.
posted by desjardins at 12:57 PM on February 19, 2010

he bought me a suitcase full of socks and a king size bed. we're getting married in 2 weeks, so i wouldn't say that grand gestures are only performed by people who in some small part of their soul realize the target of their affection isn't that interested in them.

oh - he also got all new kitchen utensils and dishes to show me that he was willing to make a home.

he might pop in here later to give you more about the thought process.
posted by nadawi at 1:29 PM on February 19, 2010

I've pulled off romantic gestures successfully on several occasions but I think the key to that success has been making them the opposite of grand gesture cliches. So in the very early stages of a relationship, not before it has started, spontaneous not planned, smaller scale rather than grand (so aiming to avoid the other person being left feeling awkward), responding to something you know about than rather than relying on cliches.

So this doesn't fit your exact description, but it is an example of realistic things.

A couple of examples.

I once found myself awake ridiculously early in the morning so I got up, and on the spur of the moment, hitched-hiked out of town to turn up on someones door step with flowers and breakfast. What this wasn't: champagne and roses. What it was: croissant and jam form the local shop, and a bunch of crocuses (so no big bunches of roses but something small that wasn't going to end up dominating room, and flowers that related to her taste in things). What I did: turned up, made breakfast, eat it with and then left promptly so she could get on with the rest of her day without having it disrupted.

In the very first days of my relationship with my now wife we went to a museum together and on the way out I tried to buy her some jewelery without her noticing to surprise her outside. She noticed me doing it but it made no real odds. The thing was this was a ten dollar resin bracelet with dead bugs embedded in it, so she wasn't going to get embarrassed by the amount of money I had spent, and I had made a shrewd guess she'd get a kick out it -- in her words "it showed you had a bead on who I was".

To answer your specific questions:
What were you thinking and feeling as you planned it?
It's always been spontaneous so I have never had too much time to build a big picture up in my head.

Did you have a specific vision of how it would go and how she would see you?
No, see above. If anything I've tried to avoid this.

How were you hoping she'd react?
Easily, in a relaxed fashion. As I've said avoiding potential embarrassment is important -- you might want some to blush, briefly when you surprise them with flowers, you don't want them trailing down the street afterward looking awkward at having to carry such an obvious romantic cliche down the street with them as they try and go about their business.

Did you tell your friends what you were planning to do, and what was their response?
No just did it. It needs to be about the other person not you. Why does anyone else need to know?

What was her response to the event? Its always worked pretty well, never really fallen flat on its face. A lightness of touch is what seems to do it.

Have you ever done something like that a second time? Yes, but because I've made it work successfully by avoiding the cliches.
posted by tallus at 1:32 PM on February 19, 2010 [2 favorites]

Before we were together, my partner and I had kinda been circling around the whole issue for a while, so for valentine's day I wanted to do something which left my intentions in no doubt whatsoever, and would also hopefully demand a response (positive or negative, I just wanted to lock something in by that stage!).

I'm not exactly messy, but I'm not meticulous - and it's well known that I truly suck with cutting, pasting, fine detailed stuff like that.

So, in an effort to at least somewhat subvert valentine's day stereotypes, I ordered a pile of pink paper, and proceeded to make a bunch of origami roses for her, scented with rose oil (actually, I proceeded to fuck up, over and over again, and then buy more paper, and then make the frigging roses). I knew she would appreciate the effort, being well aware how totally shithouse I was and am at things like origami.

It wasn't grand like fireworks, and I didn't want it to be. I just wanted to do something which said, "I think you're unambiguously fantastic, and I'm prepared to spend hours over weeks doing something I'm not good at and don't particularly enjoy just cause I'd like to make you happy" - which I think is a pretty good thing to know about someone when you're going into a relationship.

It did the trick.
posted by smoke at 4:28 PM on February 19, 2010 [2 favorites]

When I was in a long-distance relationship with my now-wife, she made me an amazing homemade cheesecake and flew halfway across the country with it on her lap to surprise me for my birthday. It worked.
posted by The World Famous at 4:36 PM on February 19, 2010 [2 favorites]

Everything iamkimiam said. Is your guy trying to win her over - or does he want to have real fun and share a fantasic, playful, childlike side of himself? There's a real intimacy to goofiness.
posted by Lesser Shrew at 5:36 PM on February 19, 2010

Response by poster: I didn't want to make anyone feel self-conscious, so I left out the details of the character/story. This guy is fairly emotionally immature, and the grand schemes he plans don't work. He's never had a real relationship, and he keeps doing these huge things because he hopes that they'll help him win over women he likes. I'm looking to get inside the heads of people who do over-the-top, unlikely things to try to win a woman, and to figure out what the thinking is behind these unusual actions.

I hope this doesn't make any of the people who have written feel uncomfortable, because your stories are all very touching and extremely helpful to me. But the guy I'm writing is a bit of a bumbler. He doesn't have a girlfriend, and the wacky schemes he plans in order to woo women tend to get in his way. I think that the way he thinks about women, the fact that he (as someone put it upthread) uses big plots in lieu of communication, is really interesting. So I was hoping to get some perspective on how people think about this sort of thing as they're planning it and in the aftermath of the events. Again, sorry if that hurts anyone's feelings, because your stories are incredibly sweet.
posted by decathecting at 9:37 AM on February 20, 2010

No offense taken. Just have your character do what we did, but in reverse order! (Like, before there's a relationship. Or a restraining order.) ;)
posted by iamkimiam at 9:58 AM on February 20, 2010 [1 favorite]

Best answer: ocherdraco pretty much nailed my thought process. I am also a woman and I was doing it for a man.

I made a big birthday cake. For someone who didn't want it. For someone who told me they didn't want anything for their birthday. For someone who, in fact, refused to even admit to having a birthday.

Thinking: I'm really obsessed with this guy, I wish he would like me back. Also I thought about lactose intolerance and types of icing. And how to transport a cake (it's kinda difficult to buckle a cake in securely). And when to make the cake--I got up super early to make it day of for maximum freshness.

Vision/hoped for outcome: I hoped it would end not-badly. I did have dreams of running off into the sunset together, but I didn't really expect them to happen. I was definitely hoping for a really heartfelt thank-you or something, though.

Accomplices: None.

Actual outcome: He didn't eat it. He took it back to his dorm and gave it to his dorm mates. He did say thank you. But only while making it clear that he wasn't going to eat any of it. I suspect he was ticked because he didn't want to feel old(er). I was crushed because I actually worked really hard on the damn cake and I never got a real acknowledgment of it.

Did I ever do this again: No. A thousand times no.
posted by anaelith at 12:39 PM on February 20, 2010

To be very, very clear:

Life does not work like romantic comedies. Romantic comedies lie. Romantic comedies sell a world that is not our own. It's a silly world full of hapless dudes and the ridiculously hot girls that love them.

This world does not exist. Do not forget this.
posted by effugas at 11:14 PM on February 21, 2010

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