And Now, Your Worst Failed Romantic Gestures

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Back in eighth grade, I fell in love with a girl who didn't want anything to do with me, and the lovesickness got so bad that I played up the friend angle and called her every night, hoping and praying she would change her mind and want to hook up with me (NOPE). Anyway, I've told this story before, but one night while I was wooing her, I serenaded her over the telephone with "Don't You (Forget About Me)" by Simple Minds. All of it. I may as well have read the entire script from The Breakfast Club while I was at it. The poor girl. I hope she went and got a sandwich while I was crooning into the receiver.

Men have often been accused of being unromantic, and the reason most of us are this way is because, 90 percent of the time, any kind of grand romantic gesture on our part ends with the woman being utterly terrified. "Aw, that's so sweet! [Runs.]" I have serenaded women. I have purchased a single red rose on a first date (I planned a picnic; she brought a friend at the last second). I have made mixtapes. I have written bad poetry. You name the flesh-creeping romantic gesture, I have attempted it, only to see it end in catastrophic failure.


And I'm not alone. Witness now the poor souls who attempted to pull off some dipshit "Cameron Crowe movie finale" action, only to have it go spectacularly awry.


Junior year of high school, I hooked up with a girl who had a boyfriend at the time, then decided the right thing to do was convince her to date me instead. My study hall was in the same classroom that she had a typing class or whatever, and everyone in that class was assigned a cubby with a name tag for the teacher to fill with graded assignments and such. For a few months, I would print out shitty emo lyrics (sooo much Brand New), bold the parts relevant to our relationship or add a personal message, and slide them in her cubby.

We actually did end up dating, and I asked her if she was getting my messages. She had no idea what I was talking about. Turns out the cubby that her paperwork went into was above, not below, her name tag. So for a few months of his junior year, some random guy with an alphabetically similar name to the girl I was seducing received random anonymous song lyrics/love notes trying to convince him to leave his boyfriend.



Let's just say this mixtape included me singing over (because I had the ultimate mixtape setup for the early '90s!) Taylor Dayne's " Love Will Lead You Back," with special alternate lyrics just for her.


I didn't just make her a mixtape of all the love songs that said all the things I wanted to say. I also typed up an explanation for why I chose all of those songs—you know, so she could see how much thought and effort I put into it. The one song I wanted to highlight was Wilco's "Forget The Flowers," so I decided to take it a step further and type up the lyrics to all the songs on the mixtape. This was very early internet days, so I couldn't just cut and paste the lyrics onto a Word document—I had to spend an embarrassing amount of time listening to the songs over and over again so I could write all of the lyrics down before typing them up.

Needless to say, this failed miserably, and I decided to spend the next year trying to smoke enough weed to bury my embarrassment.



My sophomore year, I had a crush on a senior girl, a friend of a friend. The year went by without my seeing much of her, but at the end of the year, I finally managed to get some face time when I was invited on her senior trip (we were at opposite ends of the same friend group). It meant a week on the beach in North Carolina, plus a 12-hour drive there and back, to see if there was something there. We had a good time together, but long story short, I chickened out and never actually got to make a move. We went back to campus, she graduated and moved home, and I figured I'd never see her again ... until a couple weeks later.

I got a padded envelope in the mail, with a burned mix CD inside, and drawn on the CD, a picture of us from the beach vacation. All the songs very clearly emphasized themes of "I miss you," "I love you," "Wish you were here," etc. etc. I kicked myself for not making a move when clearly the feeling had been mutual, but then a few days later, I found out she'd be back in town for 4th of July weekend. Determined not to chicken out this time, I spent a week making a similarly romantic mix CD and sent it to her at home with an inside-jokey gift.

Finally, 4th of July rolled around, and I was pretty excited to see her. An hour or two before she was supposed to arrive, I showed up to the apartment where everyone was hanging out, and was surprised to hear a song from her mix on the stereo. I went over to the stereo, and found an identical copy of the mix sitting on top of it. She had made 15 copies and sent them to everyone on the trip, and needless to say, I was the only one who had responded with a mix of my own. Heartbroken and humiliated, I proceeded to crush a pair of 40s and perform a Mariah Carey song at karaoke. I'm sure that showed her.



Back in 8th grade, I liked a 7th grader named Carlee. I wanted to impress her, so I went and wrote a two-page (front/back journal paper) poem asking her out, detailing how pretty I thought she was and what I liked about her. I placed said poem in her locker and awaited a response via MSN Messenger (this was 1998) that night.

That evening, before I could hijack our single home-phone line with our dial-up internet, my sister came bursting in, giggling. My mom was preparing supper. I asked what was up, and my sister said, "Nice poem, LOSER!" She was best friends with Carlee and had apparently memorized my early attempt at romantic poetry. She then recited the whole poem to myself and my mother, who had a look of embarrassment for me, as well as a look of pride at her son being such a romantic.

Carlee promptly told me "no thanks" later that night. That was the extent of my romantic-poetry career as well.



I was in high school and was courting a girl that I was enamored with. Her birthday was coming up, and I had the best idea: I would set up a picnic at a nearby lake with a very nice home-cooked meal, and have my friends go out and set it up while I picked her up and took her out. I had balloons, flowers, and a delicious Italian meal, and my friends were all set to take it out to set it up. As they were leaving my house with all of the stuff, I had to run to a physical-therapy appointment, and then I was off to pick her up.

As we were both leaving, I was following behind my friend when I saw the balloons fly out the window. Fortunately, they were attached to the flowers, so I knew they weren't going anywhere, and I thought my friend was just fucking with me. Turns out, my buddy rolled his window down and the balloons flew out; he tried to reach out and grab them at the same time the window was automatically rolling up. To prevent his hand from getting messed up, he reached with his right hand to stop the window from rolling up ... thus leaving no hands on the wheel. My buddy wrecked his brand-new SUV into a tree at about 40 miles per hour with all of the stuff for my date inside.

I called and cancelled my PT appointment, called the cops, and made sure everybody was alright. My mom came and took all the stuff out to the lake for me while I got my friend home. I eventually went to pick up the girl and was pretty freaking shaken up about the whole thing. We finally got to the park right about sunset. Only problem was that the park closed at dark, so a park ranger came and made us leave after about 20 minutes. It was not a good day.



In high school, I had an absolutely DEBILITATING crush on a classmate of mine—and we were best friends. I was firmly, FIRMLY in the friend zone, and as a horribly shy, chubby, no-confidence-whatsoever high school male, I had no idea how to even begin to fix this. I drove her to school every day, we hung out on weekends (when she wasn't busy with her boyfriend), we went shopping together. I was essentially "one of the girls." Ugh.

Anyway, I made her the absolute worst mixtape imaginable. It opened with this. It's bad. I'm embarrassed even typing this. Anyway, I gave it to her one day at her house. She doesn't listen to it until maybe a week later, when me and some of her female friends are over. She pops it in, and every song is more sappy and lovey than the last. I see her friend give her the most disappointing look I've ever seen, which she promptly returns. I wanted to die. Of course I couldn't die on command (god, I wish I could have), and the looks on their faces haunt me to this day.


Bobby Big Wheel:

Once, after my college girlfriend dumped me, I tried to get her back by playing "In Your Eyes" to her like in Say Anything. Except that I didn't have a boom box, so I rang her bell and played the song to her off my iPod.



This was freshman year of high school, I think, and someone was having a birthday sleepover, and it was really cool because it was co-ed. At, like, one in the morning, we found this kid named Jerry sleeping (probably pretending to sleep, actually) right next to a piece of paper that had "Hannah," "Hannah+Jerry," "H+J," and all sorts of stuff like that in little hearts and shit. So Hannah sees this and approaches Jerry later and asks what the deal was, and it turns out he planted it so that she would see it and ask him out. It didn't work.



It's my 8th-grade year, roughly 1998, and I have a MASSIVE crush on a girl named Abby. Abby was popular and pretty, and I was into the theater and had a bowl cut. As is so often the case with girls who are popular and pretty, Abby was on the girls soccer team. I was in the band. I played the clarinet.

One day, I decided I was going to attend one of her soccer games. My father, who I must stress did not stop me despite knowing my intent, drove me to the game and dropped me off. I hopped out of the car, clarinet case in tow, and walked to the field, full of the kind of confidence that can only come from sheer delusion.

I stand next to the bleachers, which were scattered with the few parents who could get off work by 4 p.m., and I put my clarinet together. By this point, I had been spotted. The girls knew I was there, and they knew why I was there. Abby wouldn't even look at me.

Even then, I figured what I had in mind would win her heart, because I thought real life was like the movies.

Right before the game was set to start, I began playing. Pep songs. On my clarinet. Accompanied by nothing but the inaudible sound of a collective sad empathy from the parents and utter mortification from the one girl I was trying to impress.

Needless to say, she didn't really speak to me after that until roughly our junior year of high school. Now, as adults, we live in the same large Southern town. According to Facebook, she's married to a lawyer. I bet he never played the clarinet for her.



I come up with this brilliant scheme where I have a friend that worked in the attendance office look up her class schedule; with this knowledge, I will leave a single red rose in each class for her like some ridiculous love trail. And on that February 14, I proceed to visit each of her classes before school starts and leave these red roses with each teacher, asking them to make sure this girls gets them. Each teacher stared at me like I'm a wounded puppy in a storefront window. To top it off, I leave another dozen red roses with a note attached at her last class of the day. The note, of course, was to convey that I was the one that had gone through all this trouble to ensure that she had a memorable Valentine's Day, and that we should go out, yada, yada, yada.

Naturally, I spent that afternoon staring, praying, and begging for the phone to ring, as if it would hold the secret to curing me of my virginity ... which didn't happen. Not a sound, nothing, just this feeling of a knot in my stomach that was slowly becoming the consistency of concrete. So I get to the psychology class I share with her the next day, worried but still optimistic, to find she's not there. Nor the next day, or the one after that. Two weeks go by, and she hasn't come to class. After this, I feel like I have to ask our teacher what had happened (since of course I also left a rose in the class that I shared with her). The teacher stammers out something about how she has changed schedules and is in a new psychology class.



She was a soccer player, and one day, about a month before homecoming, the captain stands up at a school assembly and begs more people to attend the games. An idea springs into my head. A mistake. Next thing I know, two buddies and I are planning to paint our chests. We're going to go to the Saturday-morning soccer game and cheer them on. Then, afterward, I'll ask her to homecoming.

We paint our chests, and of course that day it is about five fucking degrees. We go to the game, and all the mothers think we're adorable. The girl comes up after to thank us. And of course, like an idiot, I ask her to homecoming in front of my friends and the whole girls' soccer team. "Sorry, I'm not going with a date this year, I'd rather go with a group of friends ...."

I'm so devastated, I don't go to homecoming. If I had, I would have seen her there with her date.



When I was in 6th or 7th grade, my friend's sister had turned way hot. My friend told me she had mentioned she really liked guys with shaved armpits. So my brain decided the best way to impress this girl was to hack at my new underarm hair with an old two-blade Bic razor of my dad's.

This was before the triple-lubricated Adamantium razors, so I ended up getting pretty bad razor burn. My pits were cracked, red, irritated: two red and bloody rings slashed around my white, stubbly arms.

But I didn't care. I knew if I had smooth pits, she'd dig me. I was not a smart kid.

Turns out she had never said anything about her armpit-hair preference to my friend. He had just wanted to see if I would do it, because he knew I had a crush on her. She took one look at my arms and laughed and laughed and laughed until I hung my head in shame and left.

My friend and his sister are assholes.


I was seven years old, in 2nd grade, and we'd gone to school together since kindergarten. Her name was Sarah. For my birthday, my parents took me to the local Chuck E. Cheese's for a day of pizza and games, and that's the day when I figured out my plan to woo the love of my life. My plan was to win enough tickets to get one of those rings that had the birth stones in it ... I eyed the one with the ruby. So I spent all $5 of my spending money playing some game and totally sucking at it, not getting enough tickets to win.

A couple days later, while snooping through my older sister's room, I found the same shitty ring they had at Cheese's, only this one had an emerald and a diamond. My plan was hatched: I'd figure out a way to get her this ring. Lo and behold, a few weeks later, it was announced that our class would be taking a special field trip to that Chuck E. Cheese's for the day. The night before we went, I snuck into my sister's room and stole the ring. I then got a piece of paper, wrote a quick love note on it, stuck the ring inside, and folded up the note for the next day.

My plan was to play games all day and then pretend like I won it right there and give it to her. I told NO ONE of this plan. So at the end of the day, I pulled Sarah aside and said, "Hey I won this somehow, and was gonna give it to my sister, but you can have it if you want it." She took the letter, opened it up, and without even reading the note saw the ring, threw the whole thing on the ground and ran away laughing. She told EVERY girl in class, who all then of course came up to me and asked me if it was true, which I of course denied. It was never spoken of again, thank god. And I've never told this story to anyone, somehow.

Also, my sister was really bummed that she lost her ring.


In 6th grade there was a girl named Elizabeth Meldus. At one point, I found a letter in my locker from her that began, "My Dearest Andy ... "and my heart skipped a beat. I was so excited I couldn't bring myself to read her note, and instead just stuffed it in my pocket before heading to humanities class with a spring in my step.

Heart pounding, I unfolded the letter with sweaty hands and began to read.

"My Dearest Andy, I got your letter ... "

I will pause here to mention I had never written Elizabeth a letter. As would be revealed later to much laughter, my asshole little friends had written Elizabeth a letter in which they pretended to be me. They began their note "My Dearest Elizabeth" and then complimented her intelligence and giant rack and asked if she'd be my girlfriend.

The romantic gesture wasn't actually my own, but the failure was all mine. I read on.

"My Dearest Andy, I got your letter. I would never go out with you because you are so gross. -Elizabeth."



I was seeing a girl at another college. When spring semester started, she abruptly stopped talking to me and didn't answer my phone calls or texts. I decided that in order to compel her to call me, the situation called for a romantic gesture.

So I sawed a tennis ball in half with a bread knife and put a small passport-sized picture of myself in the center of the tennis ball. I put it in a box with packing peanuts and NO NOTE and mailed this menacing little love trinket to her. It was not intended as a threat. Everyone I tell this story to says it is weird and creepy and stalkerish. Never occurred to me. I really had a gut feeling that this would get our relationship back on track.

A few weeks later I got her to talk to me on the phone. I was disappointed to find that her response to the sawed-in-half tennis ball was mostly confusion. So that was that. Never heard from her again.



When I was in 4th grade, I wanted to give my girlfriend something for Christmas before the holiday break. This posed several problems, because I had no money and was obviously not old enough to drive anywhere to get anything with my no money.

So what do I do? I find a picture of me to give to her. Except I was a goofy-looking kid, so there weren't many "normal" pictures of me. The best I could scrounge up last-minute was a picture of me lying down next to my dog underneath the Christmas tree. However, the picture of me lying down is awkward and stupid, so I started to cut the picture down to make it less awkward. By the time I had completed it, I had trimmed everything but my face. I literally took a standard picture and cut it to the size of a thumbnail of my face.

The next day, at school, we're getting ready to go to our classes. I'm not even in her class, but I run over to her as we're about to go our separate ways and drop my face picture right into her shoe. She still had her boots on and was going to change inside the classroom. She got the classic "thumbnail-face-picture shoe-drop."

We broke up before the end of the day.


When I was in 9th grade, I met a girl at a church dance that I was obsessed with and then spent the next two weeks calling her every single day. I took her to an Avril Lavigne and Simple Plan concert where I tried and failed to even hold her hand. She started dating someone the next day. That afternoon I called into the local Top 40 radio station and asked them to play something "that will make my heart stop hurting."



Fifth grade. I am madly in love with a young lady who shall remain nameless. Finally, unable to contain myself, I write a very bad "roses are red"-style poem professing my adoration, carefully seal it up in an envelope, write her name and address on the envelope, and get a stamp from my mom.

Then, because I am scared that something will go wrong at the post office, I decide to PUT MY RETURN ADDRESS on the goddamn thing. She receives this "anonymous" letter, mentions it to her mother, and her mother — knowing my mother — goes "Oh, that's Chris's address."

She doesn't speak to me for six months, and her first words to me when she finally does are, "Why did you send me that stupid letter?"

BONUS: I also enclosed in this envelope a small clay heart I'd made. It was pretty brittle, and as an adult I am absolutely certain that it was utterly destroyed in the mailing process. So in all likelihood, before even reading my proclamation of love, she probably had to dump a bunch of red-brown dust out of the envelope, no doubt lending a sort of "this document was exhumed from an Egyptian tomb" feel to the proceedings.



We had been dating for about two weeks, and unfortunately, it was about two weeks before Valentine's Day. So, naturally, being a horned-up hopeless romantic at the time, I decided to surprise her with flowers on Valentine's Day.

The stage was set, and I went and bought a dozen red roses, which costs a fuckload of money to a poor college student. I drove down to the school library around 7 p.m. or so and looked around for her, because I didn't want to lead on that I was going to be seeing her that night or plotting anything. She was on the 2nd floor, so I walked up to her and handed her the flowers and said, "Happy Valentines Day!"

She looked at me with the most disappointing, awkward, fuck-off look, and just gulped and mustered a "thank you." At this point everyone around us literally stood up and started staring at both of us. A few people yelled out, "Kiss her!" and other shit like that. I smiled at her and went in for a kiss only to be denied. She then hugged me and essentially told me to leave and that she would call me later. A week later after ignoring me she fucking dumped me because we were "better friends" ... I'm still actually friends with her.



Fourth grade, around 1998: My mom took an extra job that made her work till past school hours, so I had to do some sort of after-school activity. These were school-run activities and not much to choose from, since my mom took the job late in the signup process. The two remaining options were pottery and nature-exploring. So pottery it was.

For the longest time, I'd had the biggest crush on this girl Kristen. I was this nerdy short guy with a mushroom haircut and thick, round glasses, and she was the HOTTEST girl in school. I never spoke to her ever unless we got paired together in gym class or something, and even then it was just strictly "hi" and "bye."

So bored out of my mind in pottery class, I thought, "Hey, know what this girl would love? A tie-dye mug!" Girls liked that Lisa Frank garbage back then, so this would be perfect. It took me two weeks to make and paint the mug. It looked awful. It was this brown-colored mug, and I tried to make tie-dye by splattering red and blue paint on it to make purple, and it ended up looking like unicorn jizz. I finally mustered the courage to give her the mug on Valentine's Day that year. I wrote a note about how I always thought she was cute and that the mug was a gift and that I would really like to hold her hand one of these days. She read the note, looked really confused, and gave me the mug back and ran off to friends on the other side of the classroom and laughed about it.



She went to a movie with some friends, and I thought it would be romantic to buy a rose and put it on her car while she was at the movie.

While I was placing the rose on her car, the movie ended, and everyone streamed out of the theater. I jumped into my car, but was stuck. Couldn't get out of the lot without being seen.

I hunched down low in my seat, and poked my head up just enough to see her coming out of the theater with SOME OTHER DUDE! I was pissed, and gunned the engine, tearing out of the parking lot, scattering blinking moviegoers, and knocking over two or three bicycles on the way out. Someone wrote down my plate number, and I had to go see the county sheriff about the bikes. Cost me two weeks of baling-hay money to pay for them.



Third grade: I had a crush on a girl named Erin, and she refused to be in the same area as me. It made me super sad if I was playing foursquare or anything near her, because she would literally run away. I thought the best thing to do would be to walk up near her while not saying anything after I made her a sign that said "Will you be my friend" on it. So I made the sign one day and brought it to school, ready to unleash it and finally be friends with her. I brought it out and she screamed (a little dramatic, I thought) and ran away. No joke, she switched schools within a month. The next time I saw her, I was 14. She remembered who I was and ran away again.

Tenth grade: We had candygrams at my high school, which is by far the most terrible idea for teenagers with big ideas about grand romantic gestures and no sense of slow, normal dating-escalation patterns. I bought a candygram for a girl named Sheila for every single one of her classes, all addressed to her from a secret admirer. Let this be a note to any youngsters reading this: No one really likes a secret admirer. It's creepy. So throughout the day, poor Sheila got a candy lollipop in every single one of her classes, embarrassing the hell out of her, with no real clue as to who was giving them to her. My plan was to show up at her locker after lunch and give her a rose and ask her to a dance. When she saw me coming up the hall with the flower, she turned away from me and refused to even look at me as I asked her out. She wasn't even able to mutter a no, as she quickly scurried away, and I retreated.



Years ago, at Christmas, my friend Brian decided he was going to propose to his girlfriend. They'd been dating for almost four years and were in their mid-twenties—the time when some folks decide to settle down, while others are just getting things sorted out.

He does the big romantic thing, and after gift after gift after gift, he brings out a GIANT teddy bear. Like the kind that is as big as my 6-year-old. It is, of course, holding a box, which inside has another box, and another one, etc.

In the smallest box, there is an engagement ring.

She looks up at Brian and says immediately, "OH ... I'm not going to marry YOU."

It was that emphasis on the last word that did it, as well as the fact that it was a completely instinctive response, no time to think about it, etc. They broke up that night.

This happened maybe 15-20 years ago, and I think about it at least a few times a year. My understanding is she got married a year or two later, and the last time I saw Brian, he was still single.



A little over a month ago, on December 8th, my girlfriend and I celebrated our three-year anniversary. Being that I'm from New York, I've always loved two big New York teams, the Giants and Rangers (I don't like baseball, and fuck the Knicks). We live in Poughkeepsie, so my girlfriend decided that she would surprise me by having us take the train down to the city to spend the day walking around and seeing the sights, going to my favorite restaurant which is right across from Madison Square Garden, and surprise! During dinner she pulls out two tickets to that night's Rangers game against the Penguins. I commence the flurry of I-love-you's and kisses, inhale the remainder of my meal, and like a giddy child, begin to speed-walk across the street to the game.

We make our way to our seats, and after the first period is up, I decide to make my move. My girlfriend went to the bathroom, so I reach into my coat pocket and pull out the $500 claddagh ring I had bought her from Kay Jewelers, complete with her July birthstone, a ruby. Her bathroom break runs late, and the second period has begun. Not long after, a Penguins fan stands up and starts getting cocky at all the Rangers fans behind him. One man, who just so happened to be sitting behind me, begins to hurl insults back at him. Things heat up quickly, and before I have any chance to react, the two begin jumping over seats to attack each other, and in the ensuing madness, the guy behind me punts the ring out of my hand, where it gets lost in a sea of drunken revelry.

My girlfriend finally shows up after the dust had settled, only to find me looking through the seats below us for this ring. I ended up not being able to find it, and she now believes that I forgot to get her anything for our anniversary. I had to ask my brother to loan me money to buy her a new one for Christmas.

To the Rangers fan who kicked the ring out of my hand, fuck you. You owe me 500 dollars. And I'm glad you lost the fight.


Drew Magary writes for Deadspin. He's also a correspondent for GQ. Follow him on Twitter@drewmagary and email him at You can also order Drew's book,Someone Could Get Hurt, through his homepage.

Illustration by Tara Jacoby.

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