Boys Share The Stupid Thing They’ve Done For A Girl They Instantly Regret

Ask anyone and they will tell you that men will do just about anything to impress a beautiful woman. They’ll drive faster than they should, buy things they can’t really afford, get into fistfights with their best buds… you name it. Sometimes, these attempts actually succeed. More often, however, they end in apathy or outright disaster.

Men often aren’t thinking that clearly when they come up with ways to try and get the attention of a lovely lady, so their plans are not always the smartest. The results, therefore, are sometimes not what they hope for at all. The stories below are of times when a man did something foolish to try and impress a woman, and instead of getting her number, he just got regrets.

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

#1 The Night We Don’t Mention

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 three are all still friends but we never, ever discuss that night.



Birthday Creepiness

This girl I really liked ages ago didn’t really know who I was. I gave her a Wii for her birthday and it was probably the creepiest thing ever to her. I thought it was a sure fire way to win her heart, get married and all that Disney magic. Fifteen-year-old me was stupid. I had just lost $400 and all of my dignity with that whole failed attempt.


#3 The Wrong Ring

When I was 16, I wanted to buy my girlfriend a ring for her birthday. I had been working and saved up some money. 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 and had 70% off diamond rings! What an amazing deal, I thought. Why not get a diamond for the same price?

Fast forward to her birthday party and she’s opening her gifts in front of her entire family and friends. She opens my gift and immediately lights up, putting the diamond ring on her ring finger. 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 gonna kill me right there, but after telling them what happened and a lot of convincing, they finally realized how funny it was. I exchanged the ring the next day.


#4 Skippy!

In high school, I saw a girl I liked walking with her friend. My genius brain decided I needed to impress her so I started skipping backward and said, “Better get to class.” I attempted to turn around while skipping and almost fell on the ground face first, but luckily I caught myself. I sped walked to class and never spoke to her again.


#5 A Fishy Funeral

My girlfriend of several months called me up and was sobbing incoherently. All I could make out between the gulps of breath and wailing was that someone had “passed away.” Her grandmother was not well, and she and I would go visit her from time to time so I assumed it was her grandmother. I threw my Xbox controller mid-game at my roommate, leaped to my feet and said, “Hey man, I have to GO!”

Once I arrived at her apartment and calmed her down, I managed to ascertain that it was not her grandmother who had passed away, but her goldfish. She said she wanted to have a funeral for her fish. I was annoyed but determined to compassionately help her cope because obviously, that goldfish MATTERED to her. I recommended she go get cleaned up and take a hot shower to relax, and while she was in there I called up a couple of my friends, and some of her girlfriends.

I had a buddy of mine go to the park at the small campus lake and dig a fish grave. I also had her girlfriends take her out to lunch. That’s when I got the floating carcass out of the bowl, wrapped it in toilet paper, and placed it in a jewelry box coffin. We went and had a full fish funeral with music and speeches by the lake. Afterward, when we were back at her apartment, she said, “I don’t know why you did that, we should’ve just flushed it.” We broke up a few weeks later.


#6 Love Foiled By Tasty Chicken

I took her to a Chick-Fil-A rally to protest their anti-LGBTQIA+ policies. Unfortunately, it was a windy afternoon and when I opened my passenger door to let her back inside my car, the breeze caught a Chick-Fil-A wrapper that had been hidden under my seat. I had been foiled by my love of their chicken yet again!


#7 Long-Term Life Ruining

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 four 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 —the 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!

I got her straight As 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… It cost me about eight years of my life playing catch-up.


#8 Movie VS Life Romance

My friend and his girlfriend of three months broke up before she went to study abroad. He told her they could do long distance, but she said she wanted to enjoy her time. She went to Europe and he emptied his bank account to buy a ticket for himself. He showed up at her apartment (she had given out her address to get ‘care packages’ from friends and family).

She was shocked to find him sitting by her front door. She flipped out on him and told him that he cannot stay with her. He had already emptied his bank account, so he spent the next week and a half trying to find places to sleep. Finally, he just ended up staying at the airport until his flight. Things that seem romantic in the movies are not in real life.


#9 Third Grade Ultimatum

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.


#10 Valentine’s Surprise At Work

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.


#11 Snapping In Class

When I was around 15, I got really frustrated that a girl I had known for a while did not like me back. I was texting her in the middle of class and the teacher called me out on it. She made me hand over the phone and something snapped in me. I threw a chair across the room and hit my desk, which broke my hand. 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!


#12 Became What He Faked

I saw a really sad girl in high school. I tried speaking to her about it and she said I wouldn’t understand. But I knew she had no one else to talk to, so what did I do? I tried telling her I would understand and she wouldn’t believe me. So I pretended I was also sad. Me “opening up” to her made her comfortable enough to open up to me.

She was right though, I didn’t understand, but at least she had someone to talk to even if I couldn’t offer much help. We ended up dating for two years after both getting even closer due to all that. Anyway, she ended up turning against all her morals and everything she stood for. She turned into the people that were making her depressed and cheated on me. Anyway, I must have done some pavlova magic because now I actually am depressed.


#13 Blowing Savings

A friend of mine traveled halfway across the country to hook up with a girl. Transport and hotel ended up costing about $500 due to him booking everything last minute. At first, I kinda shrugged it off thinking that was pretty stupid but oh well… Later he confessed that in total he actually blew about $1500, which was most of his savings at the time. Apparently, he paid for everything during the few days they were together. I know that people do plenty of stupid stuff in their 20s, but wow.


#14 Not As Awesome As I Thought

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.


#31 Lady Bug Leads To Embarrassment

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.


#16 Braving Snow For A Love That Didn’t Bloom

This happened on Valentine’s Day. At the time, it was really cold and snowy, with the snow being near one meter and a half high. Through the glass windows, you could see the “violent” snowstorm easily (in my country, the weather is pretty messed up). I had a crush on a girl who was in my classroom, and since high school, I planned to express my feelings about her, I just didn’t know how.

So, that day, I decided to go through the snowstorm, buy one rose, and wait for her in class. I had to find my way through the snow to the flower shop. I finally did it. I bought that rose, the biggest and the most beautiful one that was there. I got in class, waited for her with insane anxiety (as everyone, almost, in the class, after understanding to who the flower was meant to be given, was cheering me on).

She came in and I started walking towards her, with the insane anxiety still hanging there. I gave her the rose and asked her out to watch a movie together. She said that she will “probably” come. What happened? She kept postponing our date and we never ended up going out together. I literally prepared myself like, four times both physically and mentally. She said to me, through someone I know, that she rejected me because of the bullies in my class, as half of the class started making fun of me for bringing that flower to her.


#17 Gut Instincts Are Bad For Love

I had a crush on this girl and I wanted to impress her. Funny enough, my definition of “impressing” someone involved making a fool out of myself. But one time, I took it too far and decided to pull an OG prank involving the pulling of a stool right as someone was about to sit down. Unlucky for me, that “someone” was my crush… My dumb self thought it would be funny to pull that prank on her.

Low and behold she fell, and it would’ve been great if she got up laughing, etc, but no—she ended up fracturing her arm and I almost passed out from embarrassment. The following weeks that ensued were turmoil and I got so much heck for it. BUT IT DOESN’T END THERE! After a couple of weeks of apologizing, we began talking again. I decided it was the right time to ask her out. So I did.

I kid you not, I asked her out using this phrase: “I may have broken your arm, but I won’t break your heart.” I got rejected and was made a fool for the next three years of school. A friend even went far enough to fake medical documents and put my name on them as her spouse. I was done. Moral of the story: DO NOT go with your gut instincts for anything emotional. I repeat DO NOT.


#18 Unsolvable Problems

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.


#19 Cracking Singing Voice

I tried singing Can’t Take It by the All American Rejects in front of my crush (the most popular girl in school) and all of the other popular kids in 8th grade. Three words into the song and I had a voice crack.


#20 Heart Mail

When my dad was in college, he had a long distance girlfriend that he knew was going to break up with him. He was pre-med and had access to a pig heart. Desperate times called for desperate measures. He “romantically” mailed her the pig heart to represent how he wanted to give her his heart. He did it via snail mail, in a regular box. The smells were no joke. Not only did she break up with him, but she also called the cops.


#21 Attempted Bus Romance

I gave a random girl on the bus my bank pass. I was not at all in the mood for conversation, but I didn’t want to miss out on who could maybe be my soulmate. I guess I watched too many romcom’s because I thought I’d drop a note or something. But, I had nothing of the sort on me. I did, however, have the bank pass to our house account. I never used it, but it had my initials and last name on it; enough for her to look me up on Facebook or something similar, I reckoned…

Needless to say, it was a disaster. My moment came and I had to get off the bus. She didn’t look like she was going anywhere. I tried to be smooth and pretend to drop it while I was getting off the bus, but she didn’t notice. So I got back into the bus and awkwardly handed her my bank pass, muttering something like, “Could you give this back to me someday?” I never saw that girl again. Nor the pass, naturally. All I got was this mediocre story and endless ridicule from everyone I know because this story went around pretty fast once I told some friends.


#22 Five Days Of Chaos

I wanted to impress a girl so I jumped off the side of the middle school. I broke my ankle. Got the girl. It was a whirlwind five-day romance that even Shakespeare couldn’t top.


#23 Mixed Up Boots

It was the second grade. I had a crush on her, but she was cute and I was not, so I stayed silent. But then Valentine’s Day came around and I thought I could give her something, from a secret crush. So I got a fluffy teddy bear and some chocolates and hid them in her boots (in the locker room outside of class). Except, she and a friend of hers who had the same boots and I put the gifts in the wrong boots.

Not only that, but it turned out I was the only one who even knew what Valentine’s Day was (it’s not as popular here as it is in the States) and the girl who actually got the gift was perplexed. She went to the teacher and actually cried, I had no idea what was going on in her mind. Then, a year later, my crush on the girl faded when she cut her hair short. Oh, childhood.


#24 Used For Jealousy

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.


#25 The Diary Plan

There was a cute girl in my class. Nerdy me put her on super high pedestal mentally, but I had zero confidence and couldn’t even look her in the face directly. So what did I do? I created a “diary” where I put down my “private thoughts.” I wrote entries for a few days, including thoughts where I just happened to think about her and how cute she was.

I casually mentioned to classmates that I had a diary. A few days later, I “lost” the diary. Of course, I went around asking people, including the cute girl whether they’d seen my diary. Then, I put the diary into an envelope and sent it to the cute girl with a typewritten note saying something like, “You’ll be interested to know what this guy thinks of you.”

I thought a few days tops and the girl would be enraptured by my honest confessions in the diary and come talk to me. Nope, she never did. I don’t know whether she ever got the diary at all. Or maybe she was super creeped out by the whole thing. I spent years afterward cringing at the thought of what I did. Infatuation can make you do some crazy things.


#26 Accidental Criminal For Love

I “ran away” with her. We were in high school and I had just moved across the state, roughly eight hours away. We were dating for roughly two years, so this was a heavy blow. The reason I put “ran away” in quotations is that we came back two days later, and I never actually planned on running away forever. My plan felt like a good one at the time, and I still think it would’ve worked if things didn’t mess up as badly as they did.

We were heading towards California when she texted all of her family saying that she was running away with me. She also grabbed my phone to text my family for me, all while I obliviously drove. Naturally, our parents flipped. They called the cops and, because of laws and her parents, I was technically kidnapping her. Oh, that doesn’t sound bad enough?

I had just bought the car we were using a few days earlier, and I didn’t transfer the title yet because the car was owned by an acquaintance who agreed to let me use the car after giving him a down payment. So, I accidentally committed grand theft auto as well. The girlfriend took the SIM cards out of our phones so when I rolled up back at my house a couple of days later, I didn’t realize what kind of storm I was walking into. She did tell me that she told everyone we were running away, so I stupidly decided to just leave the SIM cards out while we were heading back.


#27 Public Letter

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.


#28 The Ugly Quilt

I sewed a girl a quilt when I was in 9th grade. I asked her for her favorite colors without telling her why. Her colors were orange, brown, and yellow. This was the first quilt I had ever sewn—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.


#29 A Harder Landing

She crashed her bike going down a paved road so I did the same to impress her (or to make her feel better, I really don’t know my reasoning). She landed in the ditch. I did not.


#30 Just Didn’t Want A Relationship With Him

I had started dating this girl that had recently broken up with her boyfriend. Valentine’s Day was about a month away, so during the time we where dating, she was dropping all kinds of hints for things that she wanted. I took note and had saved them all. So fast-forward to Valentine’s Day—I had made a public display with the balloons she had asked for, and I got her roses plus a ton of snacks. Pretty much everyone we knew had seen this happen. About four days later, she texted me and told me she didn’t want a relationship but got back with her boyfriend instead.


#31 Gift Well-Blocked

She told me she needed some time to think. After a week, I gathered a basket, put flowers, chocolates, toys, and treats for her cat in it, and wrote a heartfelt letter about how I felt about her in it. Then left it on her doorstep. She blocked me on her phone. After that, we never talked again. I checked her social media and she had already moved on to another guy, just a few days after I dropped off the basket.


#32 Hot Sauce Isn’t Hot In An Attractive Sense

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.


#33 End Of The Ride

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.


#34 Money Well Wasted

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.


#35 Successfully Bad Conversation

The stupidest, most ridiculous thing I ever did was say “bless you” to a girl who hadn’t sneezed because I, for some freaking stupid reason, thought it’d start up a conversation. It did. The conversation went:

“What? I didn’t sneeze.”

“Oh… my bad.”


#36 Started A Terrible Habit

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.


#37 Showing Up Unannounced

I knew a dude who drove 14 hours to see his college girlfriend of two months at her family’s house in New Orleans over Fall break. She didn’t invite him and he thought she was rude for being upset since he drove so far to see her for the weekend. Her family was freaked out since she was a freshman and had a dude follow her for a four-day weekend.


#38 Didn’t Even Get To Sleep On It

Not me, but this guy who liked my sister. He really wanted to woo her so he took her mattress shopping. He bought her a top-of-the-line $6,000 mattress with all the bells and whistles. She didn’t hook up with him, but she sure screwed his credit card debt. It’s kind of his fault though—he didn’t have to get her a mattress just to win her over.


#39 Seemed Like A Good Idea At The Time

I once pretended to be intoxicated and flirted with my girlfriend’s best friend to try and make her jealous. Because of that, she said that I wasn’t who she thought I was and she stopped liking me. I wanted to make her think I was cool but instead, I made her think I was a jerk. My reverse way of thinking really screwed me over with that one.


#40 Bear Bought… And Returned

In high school, this girl who I was close friends with (but also had a not-so-secret crush on) told me once how she really loved those HUGE seven-foot-tall teddy bears, so I told her one day I’d buy her one and she laughed, writing it off as a joke. Fast forward like three years and we were off to the same local college. We reconnected after slowly drifting apart.

She told me one day that she was sick, so I did the only logical thing. I drove to Costco after class, dropped $200 on that huge teddy bear, stuffed it into the backseat of my tiny Honda Civic, then showed up at her front door. She said it felt too weird and romantic given our past, so I did the whole drive back and returned the bear.


#41 Serving Her Prison Time

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?” He replied, “No man. I’m going to prison. I have to report for sentencing tomorrow.” My heart stopped a bit. “Oh, yikes. I don’t mean to pry, but what for?” I totally meant to pry because I wasn’t about to have a potentially dangerous criminal 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 gonna 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, she says.”


#42 From Regrets To Wholesomeness

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.


#43 The Best Bowl

A girl who strung me along for like two years in high school admired the nice bowls I was turning on the lathe in woods class. I made her my biggest, and best one yet. Like fruit bowl size. It took weeks. I’m convinced it got smashed because she didn’t care about me. It was amazing. Cherry, walnut and ambrosia maple.


#44 Not The Country Of Love For Him

I fell in love with a French girl through phone at work, I’m Swedish. She worked second line support and we started flirting for a bit. I told her I wanted to see her and that I would 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. Then she ghosted me. Still a pretty decent vacation.


#45 Won The Bet, Lost The Girl

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.