We often find ourselves wishing there was some kind of magic formula out there that we could use to make the mystery of love easier. If there was such a magic formula though, we’d all be missing out on the hilarity that often ensues from the crazy, outlandish, and nonsensical gestures we execute to try and impress our prospective love interests. These moments may not be very funny in the moment, but they sure as heck are in hindsight!
Here are 42 hilarious stories about the stupidest things people have done to try and impress a crush.
42. He Stopped Loving Her Today
I pretended that I enjoyed country music. Never again.
41. Common Lack of Interests
Back in college, there was a girl who lived across the hall from me who was drop-dead gorgeous. This was when iTunes library sharing was popular and pretty much everyone in the hall had their music connected to the internet. Everyone on the floor could see your music library and listen to your songs. I creeped the hell out of this girl’s Facebook and music library, basically putting in every single band and song that she liked in hopes that she would see my playlist, notice that we had the same taste in music, and then, would want to date me and hook up and stuff. It didn’t work…
40. Head Over Heels
While we were both on the dance floor, I headbutted her intentionally and tried to play it off as if we just happened to bang heads. I thought that the combined experience would bring us closer together. It did not—I was just drunk.
39. Personal Sacrifice
I intentionally fell off the slide in grade four to try and attract someone’s attention.
My right shoulder still regularly hurts 12 years later…
38. Running Out of Options
I signed up for a half marathon training group so I could spend more time around him—only to then find out that his girlfriend is also in the running group.
At least I’m getting into good shape.
37. What a Croc!
I swam across a river filled with crocodiles. When we were together later, she admitted that this was the one thing that made her have second thoughts about going out with me. Don’t try impress crushes, just talk to them—even if swimming across a crocodile-filled river seems easier.
36. Securing Your Place in History
In middle school I gave this girl I fancied a necklace from one of those 25 cent machines at the store. The necklace said “Love” on it. I felt really really dumb about this for nearly ten years. About a year ago, I went and visited her, and to my surprise, I found it on a wall full of memorabilia from her life. I find it quite touching that she held on to it, even if she only kept it as a funny token.
35. A Story With a Moral
In high school, at a school of about 1,500 students, we had a homecoming pep rally in our gym which included a basketball game called Bumpout. The winner won two tickets to the homecoming dance. Needless to say, I came out victorious and, as the entire school was cheering (for some unknown reason because I was very shy and unpopular), I ran up to the guy hosting the rally, took the mic out of his hands and blurted out “Holly—will you be my date to the dance?” The gym went silent, and then all of a sudden–to my enormous surprise—a “YES!” came out of the crowd. Fast forward eight years and she’s now my wife and the mother of my two-year-old son! Sometimes publicly crazy, impulsive, non-thought-through behavior works!
Knew a guy who went to a bowling party with a girl he had his eye on.
Realised he could stick his thumb in a bowling ball and hold it using just his thumb. Thinking this would impress the girl, he held it over her head and said “Look!” Girl looks up, ball falls, breaks girls nose, blood everywhere.
33. So You Think You Can Dance
This is really horrible and stupid, but I’ll tell the story:
I used to be pretty good at Dance Dance Revolution. I owned my own Cobalt Flux (still do, in fact) and knew all of the nine-foot songs cold, and could pass Max 300.
Our freshman year of college, they had a game night very early on—I guess it was to get the freshmen to mingle a little bit. Well, just my luck, among the arcade games, they brought in a DDR machine. I was totally shocked to see it when I walked into the student union. This ridiculously hot girl from one of my classes was dancing on it. Obviously, she was doing a horrible job, like most people do who don’t play the game, but she was laughing and being adorable.
Now, instead of being the smart kid and going back to my room to get sneakers, I decide it’s a good idea to just play in my flip flops. After getting off to a great start on Afronova, I decide to get fancy and start doing spins while on the pad. I then promptly fell off of it. Everyone in the student union was watching. I was known as “that DDR guy” for the first two months of school.
I pretended to struggle with Intro to Calculus just to get the sympathy of a specific girl.
It then turned out that one of her best friends was the girl I tutored in Linear Algebra…
31. A Bridge Over Troubled Water
I was riding across a bridge and saw this hot guy taking his shirt off on the other side, so I decided to ride by to get a closer look and say hi. As I turned my bike from the bridge and onto the path, I turned too far and fell a couple of stories into the water. I entered the water through a four-foot gap between two boats. I don’t know where the guy went, but he certainly didn’t save me.
30. On the Lamb
When my younger brother was about nine years old, he had a “girlfriend” who lived in our development. Our development was right next to a farm and there were sheep. One day, his girlfriend said she wanted a sheep, so he climbed the fence, made a leash out of rope and attempted to take the sheep out of the fencing. There was a ram in the area and it started to chase him away. He managed to get away unscratched, but twisted his ankle and got yelled at by the owners. I had to take him to the owners to apologize and they said they were just worried he would get hurt and offered to take him into their farm to see all the animals.
29. This One’s a Nailbiter
When I was 12, I started biting my fingernails because I thought that would bring me closer to my crush who also had a nail-biting habit. Obviously, that didn’t work out, and here I am at 21 and still biting my nails.
28. Uninvited Pest
My first “girlfriend” lasted one month of grade six. It was a love story for the ages. It all started when she passed me a note stating her feelings for me. Hot damn, I thought! Without ever having spoken to this girl, you have won her heart—you magnificent devil you! And with that, I proclaimed her my girlfriend in my mind! In retrospect, she probably didn’t know we were now in a heated relationship.
We attended the school dance together within the same week of our newly kindled love. We had at least one dance together—things were getting heated. I followed that up the next week by doing what I believed one had to do to get the girl of his heart’s contact information—I perused the Yellow Pages and found her phone number and dwelling establishment. One day, I started walking to her place. I didn’t warn her, but when does love ever need to be alerted?
I found her house and introduced myself to her father in the driveway as his daughter’s new boyfriend. I then creepily, in that romantic kind of way, knocked on her door. She opened it and with her loving voice she said “What are you doing here? How did you know where I live?” This was a very good question—I was ready for “Hi” or “It’s nice to see you,” but not this. I mumbled some charming words of confusion to her in my ever so enchanting tone, and briskly backed up and out of the awkwardness.
I decided to play it cool and not talk to her for two weeks.
Once this was up I decided I would invoke passion back into our relationship by spreading the good word of how our love had spread. I took home with me one of the English textbooks we read daily from the classroom’s bookshelf. I spent the whole night cleverly writing wherever there was space in the book how much passion the two of us had for each other. There were hearts and initials all over the place. The next day I returned the book to its spot before class began. I was pumped everyone was going to be jealous of my love life.
No one was jealous. There was much laughter to be had, and the class (and my girlfriend) were now for the first time informed that we had been dating. She seemed to be taking it badly. It was at this point I decided I can’t be with a girl who is shocked to find out we are dating.
I did make sure to take the book out one more time—and burn it. I hope to one day collect up the courage to actually tell her we are broken up, I worry she won’t take it well.
27. Scarred for Life
I fell hard for a guy in high school but he lived far away from me. Talking with him, I found out he has a scar that he was shy about and ashamed of—he would never take off his shirt for pretty much his whole life because of it. So one day, I used a black marker and highlighted all of the scars on my body and took some pictures and wrote him a letter that said, “we all have scars—it doesn’t make you any less handsome.” Must have worked, we’re married now.
26. Make Sure You’re Sitting For This One…
When I was nine or ten I had a crush on my babysitter. I stayed up later (after reasoning with him on bedtime) and tried to act all cool and teenager-y, which included things like sunglasses, lounging around apathetically, and generally acting independent (saying that I could go places on my own, had many ex-boyfriends, etc).
25. Taking the Plunge
Freshman year of college, we got placed in “inbound” orientation groups to do team-building adventure activities, ostensibly so we would have some friends on the first day of school. Most of the activities were normal—things like bike trips, some hiking, kayaking, etc. On the last day, we kayaked out to this island on the lake to go cliff-jumping. Now, I’m terrified of water, but there was this super hot guy in my group, Kevin, who had taken a liking to me. I was only going off the 10-foot cliff, while Kevin and the other two boys went off the 40-footer. Kevin challenged me to be the only girl in the group to do the 40-foot cliff, and…I did it. And landed wrong. And broke my tailbone hitting the water. And had to kayak home.
24. Bloody Mary
When I was like ten or twelve, I hid behind a building and punched myself in the face multiple times so that this girl I liked would see that I can bleed without crying.
23. That Went Well…
I was in the gym on the treadmill a while ago, and the only other person in there was this hot chick doing yoga or something on the floor mats. For some reason, I got it into my head that I could impress her by doing a cool move to get off the treadmill when I was finished. Like, plant my feet on the treadmill belt and just kind of slide off the back.
However, I didn’t slow it down enough first, so when I planted my feet, my legs shot out from under me, I body slammed myself onto the treadmill belt, and was ejected gracelessly off the back. I picked myself up as quickly as I could, but there was really no way to play that off like I had intended it. She didn’t say anything, but her derision was palpable from across the room. I left quietly…
22. Don’t Have a Stroke
This girl I liked was pointing at something while we were sitting in a dark theater. For some reason, I decided it was a good idea to start stroking her finger.
Didn’t end well.
21. Not a Fan
I was sitting in the library at my college, reading a book they just got in about particle physics (my major). I’m just chillin’, minding my own business, when this very cute girl sits down across from me. I panic, and start to shift the book back over the edge of the table to make the cover visible, though I make it look like I’m just getting more comfortable. She looks up. So far, my plan is working perfectly. Then she reads the title. Her eyes got wide, looks at me and gives me the “WTF is wrong with you” face, and leaves.
20. Slight Miscalculation
I ignored him. I really thought ignoring him would make him want to know me more.
19. An Apple a Day Keeps the Doctor Away
In college, I stopped eating for a few months so I could be skinny in hopes he would think I was pretty. Those months were miserable.
18. Happy Ending?
Okay, so in high school, I had a crush on this girl for like two years. We both wound up in the school musical together and I was cripplingly awkward in person. Now, the director would email all of us the same letters, weekly, so I found her email address and I was gonna send her an email, but I realized that would have looked creepy. So instead I did something 20x creepier! I created a fake email account of a bisexual girl, and sent her emails that implied she had a thing for both of us.
THEN, I started talking to her in person, and asked her if she’s been getting any strange messages. She said yeah, and we started talking about it, and out of her pure unadulterated fear of this psycho stalker, she latched onto me like a… friend. Just friends. That didn’t go at all according to plan, but could’ve been worse. Then, I realized I had to make a wildcard move if I wanted anything to happen.
So, I told her EVERYTHING. And somehow, she wasn’t the least bit weirded out. We’ve been best friends for four years now, and dating for almost half of it.
17. Just Warming Up…
In high school, I was deeply in love with a girl who knew me only as the creepy guy who stared at her in choir practice. I think my most pathetic attempt to garner her affection is a toss-up between that time I made a song on a digital music program for her and gave her a CD of it, or the time we were in one of the school musicals together and I sent her a plastic rose (they were selling them to support the show) with a note on it signed “Love, [my name].” I cringe every time I think about high school…
16. Think Fast!
There was a girl I liked in summer school back in the day. I talked to her older brother and borrowed the game Keymaker from him—and got his number just in case something happened. Later on, I called their house. When she picked up instead of him, I panicked and said “I LIKE YOU” and hung up.
15. Tragic Poet
Back in high school, AOL Instant Messenger was a thing. Every morning before school, I would try to post in my “auto message” some profound statement about love or relationships often using song lyrics. I did this specifically in the hopes that my crush (who was one of my friends on IM) would see it and have some revelation about how awesome I was. Looking back, that was a lot of energy spent for something I could’ve done by just being myself around her.
14. You’re So Worldly
I pretended I knew how to read Arabic. Why? I’m not quite sure. I’m not Arabic, nor was she. I guess I just wanted to act like I knew everything. Stupid teenage years!
13. So Confused
I took the advice of a good friend of mine for this one. There was a pretty girl who usually had lunch at my dorm’s cafeteria around the same time I did. So one day, before I went to lunch, I stashed a pineapple in my backpack. I ate my lunch as usual. She came in as usual. When I was done eating, I took the pineapple out, walked up to her table, and asked her, “Do you need a pineapple?”
When she started to produce a confused rendition of the word “No,” I cut her off and said, “Everyone needs a pineapple.” I planted the pineapple on the table in front of her and confidently walked away. We never spoke again.
12. Looking Back
I did a backflip during sports class. Everyone laughed and said I shouldn’t do that, which I took to mean I didn’t quite look as cool in the act as I imagined I would. I was as embarrassed as can be.
Lesson learned. Don’t start doing random backflips, kids!
11. Lifetime Commitment
I started playing WoW in attempts to get a date with a guy I liked. I got rejected and have since lost all my free time to the evil devil game.
10. An Explosive Romance
I was talking to this girl at a New Year’s Eve party in Philly. She was bummed about not being able to see the fireworks. I just happened to have a box of fireworks in my trunk so I set them off in the middle of the room. I was lucky that it made her night…
9. Winter Wonderland
Grade 2. Stole one girl’s sweater to impress another girl. Hid it in the boy’s bathroom. Did not get the girl. Got detention.
8. Time to Start Singing the Blues
I burned her a mix CD of love songs. Her friend then asked me if I liked her, and I panicked. Trying to play it cool, I was like “Nah, that’s just the music I like to listen to.”
She ended up dating my friend instead.
7. Taking One for the Team
When I was a teenager I decided I was going to impress a girl who was a huge fan of the WWE. I grabbed a metal folding chair and proceeded to hit myself in the face with it multiple times while flopping on my back as if I were Mankind in an actual “Hell in a Cell” match.
At first she was quite amused, but soon her face turned to sheer terror. The massive beating I decided to give myself had caused my head to split wide open, which allowed for quite a show all in itself. I went straight to the hospital and received over a dozen stitches all in the name of young love.
That was the day I learned that professional wrestlers use a different type of folding chair when “performing” in the ring. The more you know…
6. Chocolate Chip Fire
When I was 16, I was hanging out with a cute girl who I really liked. We’d been hanging out for about a month or two. At her house one night, I decided to do some impressing and announced that I would cook her and her mom dinner. I decided to make a surprise dessert of chocolate chip cookies with it, and put them in the oven right as we were sitting down to eat so they’d be ready once we finished eating.
It went great, my mom had taught me well and the dinner was delicious. Afterward, she and I were upstairs having a good time (in our underpants) when all of a sudden, her mom comes up yelling “FIRE!! WE’VE GOT TO GET OUT, THERE’S A FIRE!” We jump out of bed and run outside, still in our underpants as the volunteer fire truck shows up.
Turns out it was just a smoke scare. I hadn’t set a timer because the cookies were going to be a surprise and I ended up forgetting about them. We ended up being together for the next two years though anyway.
5. Bringing Home the Bacon
This girl wanted bacon. I lived about 30 minutes away, but I picked up bacon and bacon dip and drove to her place. Turns out her and her friends all wanted the bacon. So I made bacon, didn’t get to eat any of it, and then she had to go to work.
4. Cooking Up a Storm
I put a $5 bill in her locker with a note addressed to one of her secret online screen names on a post-it. This was in 7th grade. I then talked to her for a few months online almost every single night and refused to tell her who I was, even though she continually asked. I finally told her at high school graduation, the last time I saw her, that I was “tornado.” She didn’t say a word. It remains one of the most awkward things I’ve done.
3. Very Cheesy
I worked as a counselor at this summer camp in June for about a month, and one year, there was a very attractive new climbing instructor. He was a hot topic among the other lady counselors. We had a staff orientation before the actual camp started where they held a cookout at this farm, and the climbing instructor happened to be passing out the cheese. And I thought to myself “Oh, this is my chance, I’m going to impress him and be really funny.” So I go up to him with a totally straight face and say “Cheese me!” There was no reaction, not even a smile, only confusion. And then he finally said, “Cheese please?” So I just nodded in shame and accepted my cheese. He asked for my name, and I gave him my real one, which I shouldn’t have, because he probably remembers me as that girl who asked him to cheese her.
2. The Long and Winding Road
When I was 17 years old, this girl that I was madly in love with asked me to drive her to Buffalo (a city 400 miles away from my hometown) to visit a friend. We had just kissed for the first time the week before, and I was elated to spend a weekend away with her.
So I lied to my parents, drove all the way up to Buffalo in the dead of winter, and when we arrived at her friend’s house, another guy came out and gave her a hug and a kiss.
Not knowing what to do, I said, “Give me a call when you’re done.” I drove off to the mall, watched The Ice Harvest, slept in my car, and picked her up the next morning.
I drove for 8 hours not saying a word, and listened to her try to apologize. To this day, I remain constantly paranoid that every subsequent woman I am with will do the same to me.
1. Bad Life Decisions
I took up smoking, because she did it. I would go on to only stop 12 years later after a heart attack.