February 28, 2023 | Samuel Ira

Guys Who Did Something Really Stupid For A Girl Share What Happened

Love is beautiful, but it can also be distracting. When you're infatuated with a person, it's easy to sometimes go against your better judgment. Often, while in the pursuit of love, people are willing to jump through hoops, going above and beyond to get their attention or win their affection. Sometimes it works, sometimes it doesn't.

In many cases, only hindsight can bring to light how silly or ridiculous a gesture actually was. In some cases, it ends up being worth it in the end. Other times, it just becomes a funny story to look back on with slight embarrassment. Just take it from these guys, who recently shared stories about what happened the time they did something really stupid for a girl.


Don't forget to check the comment section below the article for more interesting stories!

#1 Cut It Out

When I was 20 years old, I was dating a girl my own age and was absolutely in love with her. For Valentine's Day, I brought home a large sheet of cardboard from work and cut it into a giant heart. I bought a red sweatshirt and some various paints to make my most embarrassing outfit to date. I painted the giant heart red and cut out an oval in the middle. On the costume, I wrote, "Will You Be My Valentine?" I also painted my face red, stuck it through the hole in the cardboard, and then showed up at her job to surprise her. Fortunately, she thought it was cute.

#2 Going The Distance

I got on my bicycle and rode 18 miles to see my girlfriend. The only problem was, my girlfriend lived 28 miles away. If you haven't clued in yet, basically my tire popped at 18 miles. I had to walk the rest of the way, a full 10 miles, while lugging my bicycle behind me. By the time I got to her house, I was sweating buckets. At least she thought it was sweet.


#3 Musical Mistake

I bought a girl an iPod for Christmas when I overheard her telling someone she wanted one for gymnastics practice. I gave it to her at a friend’s Christmas party. She gave me an awkward thank you and then proceeded to sit in one of my best friend’s laps and flirt with him. I was devastated. Looking back, it was such an odd encounter and I don’t blame her if she was a little freaked out. We didn’t know each other very well at that time. We are all still friends, but never ever discuss that night.

#4 Bear With Me

A girl was leading me on, but also being obvious about it. I was stupidly believing I could change her ways and get her to actually date me. She had revealed she always wanted a giant teddy bear, so for her birthday, I bought a giant bear costume from Amazon and like, 90 roses. Creepy and cringy, looking back. Anyway, she called me while intoxicated the night before and screamed mean things at me through the phone.

I finally broke down and told myself she was a terrible person. I let myself think I could change that because I was desperate to not be alone. In the end, I created a sign that said "Free bear hugs and roses for Valentine's" and wore the bear suit onto our college campus on Valentine's day to give away all the roses.

It made so many people happy that it was one of the best things I've ever done. So many hugs and girls were crying because they didn't have to feel so alone on a stupid commercialized holiday. It was cool. Plus, the football players all took a flower and hugged me, which was surprisingly wholesome. I guess I still consider that whole situation a win.



#5 Prison Mates

I drive long haul bus routes. One time, some dude showed up without luggage to travel across the state. It was weird. I asked him:

"No bags?"

"No man. I'm going to prison. I have to report for sentencing tomorrow."

"Oh, yikes. Don't mean to pry, what for?"

I totally meant to pry because I wasn't about to have some potentially dangerous individual on my bus for nine hours. "Oh. I'm going to prison for this girl. She got caught with a bunch of illicit substances in her car. I was riding with her. It was going to be her third strike so I told the cops they were mine. I love her man. She'll be waiting for me when I get out."


#6 Perfect Prom

I had a good job that paid me a stupid amount of money, but my parents, for some reason, didn't pay any attention to what I was doing with it. As a senior, I was dating a sophomore. Her mom told her, "It's not your prom, so I'm not paying for a dress and everything." I ended up spending well over $1,500 on a dress, hair, makeup, shoes, a manicure, a photoshoot, AND a custom-made blue-topaz pendant with a massive stone I hand-picked to perfectly match the dress she would be wearing. Last time I saw that stone, it was on a chain around her best friend's neck after we broke up.

#7 Accidental Engagement

When I was 16, I wanted to buy my girlfriend a ring for her birthday. I had been working a lot to save up money for it. My plan was to get a silver ring with her birthstone and pay around $700. I went to a jewelry store at the local mall and discovered it was going out of business soon, so they were selling diamond rings for 70% off! What an amazing deal, I thought. Why not get a diamond for the same price?

Fast forward to her birthday party, when she was opening her gifts in front of her entire family and friends. She opened my gift and immediately lit up. The room gasped and I nearly passed out. I realized immediatly what I had done. I had bought an engagement ring. I thought her dad was going to end me right there, but after telling them what happened, they finally realized how funny it was. I exchanged the ring the next day.

#8 A Thesis On Regret

I was so completely obsessed with a girl that I disregarded my own well being and threw away any chance I had for success. We dated for 4 years while we were in school for Architecture. Towards the end of our degrees, she started having trouble with her thesis project and asked for help. In what can only be described as a lengthy period of insanity, I decided to stop working on my own projects and focus entirely on her thesis.

I did everything for her—designs, drawings, models, and write-ups. Her presentation went flawlessly and she had the top grades in her class. As a result of staying up all night for weeks at a time and repeatedly delaying my own work, I failed most of my classes and dropped out of school. She was grateful and begged me to help her work on her master's degree as well.

No Problem! Got her straight A's and a brand new diploma to add to her collection. She dumped me on graduation day and immediately began a relationship with someone who understood the importance of self-respect. I'm not even mad. It was entirely my own doing and I learned some valuable lessons. Really expensive screw up though... cost me about eight years of my life playing catch-up. NEVER put a school relationship before your own success.

#9 Dying For A Date

For the first girl I asked out, I left a chalk outline of a body on her driveway, along with a clearly fake police report indicating that I was dying to go out with her. She walked outside, looked at it, and then walked right back into her house. I don't think she was very impressed by the gesture whatsoever. Yeah. I still cringe at the memory.


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#10 Pick-Up Lime

I asked my girlfriend out by handing her a lime and saying it was my "pickup lime," then offering to eat the whole thing (peel and all) if she went out with me.


#11 Quite The Disservice

I had a break up that really hurt me emotionally. A short while after, another girl came along to manipulate me. We were together for a while when I decided to enlist in the military. She was upset, so she convinced me to get an apartment with her that she could live in while I was gone. Fast forward to three months after I left—I found out she opened a credit card in my name, repeatedly cheated on me and trashed the apartment. This was almost three years ago and I'm still dealing with the repercussions.

#12 Texting Trauma

When I was around 15, I got really frustrated that a girl I had known for a while did not want to get together. I was texting her in the middle of class and the teacher caught me. She made me hand over the phone and something snapped in me. I threw a chair across the room, then hit my desk. I ended up breaking my hand and I broke down crying. I thought about it today and it still makes me cringe sometimes. I apologized to my teacher and everyone included. The girl is now one of my closest friends!


#13 Fishing For Attention

I tried to impress a girl at my middle school's Fall Festival. A friend of mine bet me $60 to eat a live goldfish that he had just won. I did it, but it did not impress her. Instead, the girl started crying while screaming at the top of her lungs how terrible of a person I was for ending an innocent goldfish's life.

#14 Candy Crush

My first crush in eighth grade loved Hershey's chocolate. I always made sure I had some packed for lunch. I'd share half the bar with her always, thinking it would get her to go out with me. It worked, actually. She ended up breaking my naive 8th grade heart but we laughed about it years later. I could've eaten way more chocolate though, so that was pretty stupid of me.


#15 Committing To The Commute

I agreed to move into an apartment with her that was 40 miles away from my workplace (it was very close to her workplace). I spent two to three hours round trip in the car every day for over two years. I didn't regret it at the time, but now I have a much shorter commute and realize how exhausted I was by the terrible commute.

#16 Drowning In Love

A cute girl challenged me to race across a body of water. I barely knew how to swim and almost drowned. Two years later, the same thing happened, but with a different girl. I just never learn I guess. To this day, I still haven't invested in swimming lessons, despite those two incidents clearly demonstrating that I need them.


#17 The Toxic Flake

In high school, my classmate and I were always flirting and occasionally we kissed at parties. Then, the moment came where she left high school and I had to redo my last year due to an accident. She left for another city that was a couple of hours away to attend university. We promised we would stay in contact.

After I rehabilitated, we agreed on seeing each other in her city, but she never turned up. Up to that point, I genuinely believed we both liked each other. Normally, I would immediately break off contact, however, this girl was different. Once or twice per year, we would stumble upon each other in our hometown and we would immediately hit off with this obvious flirtatious behavior.

We continued to stay in contact through social media and text messaging. After many tries, as I previously mentioned, I made the decision to stop all contact with her because it hurt every time she ignored me. She didn't even react to it. It turned out she was a very toxic person and I'm glad I don't speak to her anymore.

#18 Doctor Love

A girl told me that she wanted to be a sports medicine doctor, so you know what? I wanted to be a sports medicine doctor too. Five years later, I was in medical school and she all of a sudden changed her career path. Yet, somehow, this was the best decision I've made. Who knew that being stupid in love could lead to a great career?

#19 Gaming For A Gymnast

I dated a gymnast in high school. One time, we went to a park and we came across a pair of parallel bars. They were designed for stretching, but I was convinced I could do a handstand on them. She kept insisting that they were too far apart, but I didn't listen. I attempted the handstand, and they were indeed too far apart from each other. I collapsed down, jamming my chest past my hands and tearing all the ligaments holding my chest muscles to my breastbone.

#20 Not-So-Lucky Ladybug

When I was about eight-years-old we took a field trip to the Field Museum in Chicago. During our lunch break, I decided to wander off to the gift shop and see what they had. I had a huge crush on this girl named Victoria in my class and I saw this ladybug ring. I knew she liked ladybugs and I had money my parents gave me, so I decided to buy the ring and give it to her.

I was really nervous and kept waiting for the right time to do it. I eventually decided to just go for it and walked up to her near the end of the trip. She was with some of her friends which made me more nervous, but I found the courage to do it. She looked at the ring and laughed. Her friends joined her and she tossed the ring in the trash.

I was completely devastated and tried hard to hold back my tears. Even though I’m over it now, that completely screwed my confidence with girls for a long time. Looking back, I may have embarrassed her too, giving it to her in front of her friends, which is why she reacted that way, but whatever the case, it’s probably the most embarrassed I have been in my life.

#21 Bad Habits

We were in high school. She was really into sodas, but her parents would never let her have any. My parents, on the other hand, were willing to buy sodas for me regularly. I would get her cases of sodas to "win her over" like the goober I was. At some point, I started getting addicted to sodas myself. It took me 10 weeks to drop that girl, but 10 years to drop that gross habit.

#22 Just Skating By

I slammed into the wall of an ice skating arena at top speed (or at least as fast as a 10-year-old could possibly go), bruising my entire body. It was a free skating period after skating lessons. There was a girl I didn't know, who was about 15, wearing a skintight tan figure skating suit covered in glittering sparkles, skating around the rink, and I was trying to follow her as closely as possible for reasons that seemed important at the time. Anyway, I obviously couldn't handle skating that fast and went right into the wall, causing minor injuries.


#23 Failing Flowers

She told me she needed some time to think. After a week, I gathered a basket of flowers, chocolates, toys, treats for the cat, and a heartfelt letter about how I felt about her in it. I left it on her doorstep and waited for her reply. She blocked me on her phone and ignored my existence anytime she had to walk past me in the hallways at school.

#24 Winging It

I ate 12 blazin’ wings, the hottest flavor at Buffalo Wild Wings, in an attempt to impress this one girl. Turns out, she was not impressed with a sobbing 14-year-old who had a face covered in hot sauce. You're supposed to finish the wings within 6 minutes, but I basically sat there for an hour, just crying my eyes out.

#25 The Mixtape Mistake

I made a mixtape of me singing cheesy love songs. I can't sing, so I have no idea why 15-year-old me thought it was a good idea. I put a bunch of classics on there and made sure to just sing from the heart. She'll appreciate that, I thought. I'll never forget the look on her face when she played the mixtape. Let's just say her facial expressions weren't pleasant.

#26 Solving The Problem

I liked this really smart girl who went to my school. Me, being awkward, never knew what to say to her, so we never talked. One day, I went up to her to try and show off my intellect. I asked her to give me her hardest math problem so I could solve it. I wasn't able to because it was a pretty hard one that I needed a calculator to solve. The people she was talking to were laughing, which made people around us look at me. Later, she went up to me and apologized for embarrassing me, so at least she talked to me.

#27 Climbing On Up

I free climbed a 200-foot cliff to impress the ladies. I got to about 100 feet where it started to get slightly crumbly. I looked down, and my left leg started shaking like crazy. So I told my left leg, if you keep shaking, we will have a problem. I got down, thankfully and obviously. I did make out with that cutie. So worth it in the end I guess.


#28 Campus Tour

After I met my college crush and got to know her better, I used to roam through the entire college every single day just to find her. I didn't want to call her so because I didn't want to look like a creepy guy. Now I look back and realize how stupid I was. I should have honestly just called her, it would have made things a lot easier.

#29 Flower Delivery

I drove eight miles in a car with nearly broken brakes to put flowers on her doorstep before she woke up (I was young and dumb). I found out late that it was all in vain as she "had been seeing a guy from her church that she went to since she was 10. At the time I met her, she was 17 and he was 37. I left her alone after that.

#30 Puppy Love

A boy I dated in high school broke up with me, but we stayed friends after. One day, we stopped at a pet store to pet the puppies. I was talking about how cute the puppies were and said, "You know, I actually DO have enough to buy one..." I was a teenage girl so, of course, I told him he should get a puppy since they were so cute. He bought the puppy, we played with it for a while, then I went home.

He proceeded to hate me for years because he said he got the puppy FOR ME. Apparently, he believed I would be the dog's owner? Thankfully, he still lived with his parents who bonded with the dog and it lived a very full and happy life with them. He still tells everyone about this girl who broke his heart even after he bought her a puppy. Also, it was my fault that he spent his entire savings on a puppy that he obviously couldn't afford.

#31 Love Sick

In high school, I had a huge crush on this girl. I found out she broke up with her boyfriend so after a few days, I made my move and asked her out. She said yes but on the day of the date, she wouldn't answer her phone. Finally, after the third try, she picked up and said she had to cancel the date. I actually went to the store, bought $20 in medicine, and drove to her place. I was greeted by her mom who informed me her daughter was not sick and was at the beach with her old boyfriend. I found out at school the next week that she only said yes to our date to make the old boyfriend jealous.

#32 Love Is My Religion

I started going to church. It was one of those new-age, rock band style churches, where people talked in tongues. Lets just say that didn't work out. I didn't end up with the girl I was going for but I did end up dating her friend for three and a half years, who was a non-church goer and gave me endless heck for trying that move.

#33 Catching Feelings, Not Flights

I was in Las Vegas and I was running late for my flight, so I rushed to the airport. Luckily, I got there with 25 minutes to spare. I sat at the front of the terminal and cooled down. At one point, I decided to call this girl I was interested in to catch up, etc. I got so hyperfocused on the conversation that I didn’t hear my name called five times and I ended missing my flight while sitting, literally, in front of the gate. I stayed overnight at the airport and caught the next flight at 9 a.m.

#34 Public Declaration

I sent her a cringy love letter on Facebook; something along the lines of: "I have never been loved but you're the first person who has ever loved me." Stupid me was still new to Facebook, so it was posted to her wall instead of being a private message. I didn't notice until a few days later when a friend of mine asked me about it. My family probably saw it too. It hurts a lot to remember and is the kind of stuff that keeps me awake at night.

#35 Warm With Regret

I sewed a quilt for a girl in 7th grade when I was in 8th grade. I asked her for her favorite colors without telling her why. She told me they were orange, brown, and yellow. This was the first quilt I had ever made. I took a class and made the quilt. It was a Log Cabin quilt. It was ugly as sin. I gave it to her and asked if she wanted to be my girlfriend. She said, "No." That was the beginning of my "forever alone" life.

#36 Rumble In The Jumble

This girl I liked in high school loved games and puzzles. I made her one of those little game books with puzzles. The grand finale was a word jumble that spelled out “will you go out with me” as the correct answer. I gave it to her at the movies and she was filling it out while we waited for the previews. When she solved the jumble, she looked over and started laughing the cruel laugh only a teenage girl can produce. She then started throwing popcorn at me until I got up and left. My friends still refer to this as “Rumble in the Jumble.”

#37 Stolen Dog

I wanted to be the hero on Christmas morning and went searching for a lost dog that belonged to a girl who had recently broken up with me. I found the dog, called the girl's dad and told him to meet me out front to make sure it was the same dog. The whole family was waiting. After he came to check, it turned out it was not their dog. Long story short, I stole someone's dog on Christmas morning.

#38 Weird Flex But Ok

I was flexing my non-existent muscles any time she was in the room. One time, I flexed so hard I burst a blood vessel in my eye. One of the many mistakes I made in school.

#39 Slippery Slope

I skied down a steep slope to retrieve a girl’s lost ski pole and ended up flopping down, tearing my ACL in my left knee.

#40 The Art Of Love

To preface this, I'm a hopeless romantic and adhere religiously to, "What's the worst that could happen?" I wrote love poems and recited them in Shakespearean fashion for my crush in high school. When that didn't work, I wrote her a song and performed it. That didn't work either, surprisingly. My worst moment, however, was when I fell in love with a French girl through phone at work.

She worked second line support and we started flirting for a bit. I told her I wanted to see her and that I'd come to France. She said, "Do it." I arrived in France to no one at the airport waiting for me. I rang her up, and she freaked out that I actually did it. She ended up ghosting me, but it was still a pretty decent vacation. Luckily, I have since then learned how to dial it the heck down.

#41 Leap Of Faith

When we were in elementary school, my friend had a huge crush on this girl. One day, he decided to ask her to be his girlfriend. He brought her flowers and a note saying, "I love you, meet me at the basketball hoops." He put the flowers in her locker (we didn't have keys for our lockers) and slipped the letter to her.

Later that day, she met him at the basketball hoops and said no, so out of sadness my friend climbed a tree and said, "If you aren't going to say yes, I'm going to jump!" Yeah, it was still a no. He eventually gave up, jumped down on his feet and twisted his ankle. She then moved to another city far away. This was in third grade.

#42 Brace Yourself

I've always been really self-conscious about my teeth. One of my front teeth is significantly pushed back, so looking at my smile from most angles it looks like I'm just missing that tooth. I dated this crazy manipulative girl for most of high school and when I was 16 I found out that braces were covered under my dad's insurance. I was ecstatic and told her right away how excited I was.

Her response was, she needed braces too and couldn't afford them, so it wouldn't be fair to her if I got braces myself. Ever the moron, I obliged and didn't get braces. always regretted it. The story has a happy ending though. I'm now 23 and five months ago I finally got them. I'm paying out of pocket, almost $5,000, but I'm so happy. As of this month, my tooth is finally almost in line with the rest of them!

#43 Falling In Love

I once intentionally fell off my bicycle to get a girl to notice me. I managed to heave myself off my bike going at a brisk pace and ended up with a bloody knee and elbow. The worst part is, it didn't even work. All I got from that experience was a couple of stitches and an embarrassing memory that is burned into my brain.

#44 Cutting It Close

I pretended to cut my tongue off with a pair of scissors and accidentally cut my tongue really bad with a pair of scissors. Second graders are dumb.


#45 The One That Went Away

I bought a flight to see a girl I was dating long distance. She booked one to visit me a different weekend. One week before I visited her, she changed her flight to a different destination for a "vacation." Two days after I flew home, she ended things with me. A couple of weeks later, I learned she had a boyfriend the whole time, who lived in the city she changed her flight to. She could have just broken up with me before I saw her so I could at least cancel my flight. I was a poor college student.

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