13 Men On The Most Desperate Thing They’ve Ever Done To Win A Woman’s Heart

Twenty20, NickBulanovv
Twenty20, NickBulanovv

1. “I was dating this girl for about four months and she was hesitant to commit because she was 25 and killing it at work. I completely respected her career focus, but I also knew that we were meant to be together. One Saturday night, she challenged me to karaoke, fully aware that I am the worst singer in the universe and that I have stage fright on top of it. Something came over me, though, and I grabbed the mic and belted You’ve Lost That Loving Feeling, attempting to channel Tom Cruise in Top Gun. I was absolutely horrible but she was smitten and we’ve been an official couple even since.”

— Gary, 32


2. “When my girlfriend dumped me last year, I went mental. I started hitting the gym twice a day and lost 20 pounds in two weeks. I stopped drinking. I also wrote her a love letter every single day for three straight months. It was the last one that did the trick. I just poured it all out on the page—how I felt about her and why she was so right for me. She knocked on my door the night she got it without any warning and it felt so good to hold her in my arms again. We’re engaged now.”

— Damian, 27


3. “I designed the most elaborate treasure hunt for my roommate because I’d been crushing on her secretly from the day we moved in together but I kept wimping out on saying anything to her face. She got home one night and I’d pasted a note on the door with a clue. I made at least 20 little notes with clever clues that led to random spots throughout our apartment and the last one instructed her to head to the bar down the block, where I was waiting for her with her favorite cocktail and a plate of nachos, her favorite snack. When she walked into the bar and we locked eyes, I could tell she was impressed and I was the happiest I’d ever been, not to mention extremely relieved.”

— Victor, 27


4. “Last year I was really into this chick I met online. Instead of asking her out directly, I uploaded this really heartfelt video of myself freestyle rapping about why I thought she was so amazing and why I wanted to take her out and uploaded it to Facebook. It went kind of viral within our circle and she responded by uploading a video of herself circling the word ‘yes’ on a piece of paper.”

— Robbie, 20


5. “This is embarrassing, but I wanted to impress this girl in bed so I could make her mine, and in my early twenties I had a lot of anxiety about my dick. So I searched the web and bought a bunch of supplements and pumps and for weeks I did everything possible to get bigger. All because I didn’t want to flop in the sack. But then I realized that if this girl didn’t want to be with me as is, we probably wouldn’t last. I asked her out and ten years later, she’s seems satisfied by my dick exactly the way Mother Nature made it.”

— Jeb, 33


6. “I’ve been madly in love with my best female friend for five years now, but I’ve been afraid to go for it because if she rejected me or things didn’t work out, I’d be crushed if that meant losing our friendship. But this coming Saturday it’s her birthday and I can’t hold back anymore. As a surprise, I made this detailed scrapbook of every single picture of the two of us that I could find and I added captions and everything. It’s a bold move, but I think she’s going to appreciate it.”

— Saul, 28


7. “Romance isn’t my thing, but when I first laid eyes on my current girlfriend—we met at a happy hour thing organized by a mutual friend—I knew I had to go full force. It was early February, and our very first date was scheduled for Valentine’s Day. I queued up a bunch of cute-funny e-cards to arrive in her inbox hourly throughout the day. Then I picked her up for dinner, old school style, with a dozen long-stem roses in hand. I even took her on a horse carriage ride through Central Park. If you want something, you can’t be afraid to put it all out there.”

— Kristopher, 30


8. “Senior year of high school, I managed to orchestrate a semi-successful flash mob that was intended to ask this girl out to prom. It was a genius move. It took so much preparation and it was kind of a mess, but it was all worth it because she loved the attention. We were the hottest couple for like a month and I finally lost my virginity the night of the dance.”

— Hans, 24


9. “I spent an entire week binge watching the Bachelor and Buffy the Vampire Slayer just so I could have something to talk about with a colleague I was desperate to date at work who loved those shows. In the end all the TV watching was unnecessary because we had so many other things in common. Two months into dating, I confessed what I’d done in preparation for the afternoon I finally approached her in the kitchenette at the office and she thought it was adorable.”

— Luke, 28


10. “As a junior in high school I moved to a new town halfway through the school year and I fell hard for this girl in my Algebra class. Since I was the new kid, no one knew I was an ace at math, so I started failing tests and pretending to struggle just so I could ask her to tutor me. My GPA took a dive so I could have a shot at hooking up with that girl, but I got to third base within three tutoring sessions and when she finally figured out that I was playing dumb just to get in her pants, she was actually flattered.”

— Taylor, 31


11. “I reenacted the ‘candle song’ from that lame Broadway show Rent for my girlfriend of a year. Musicals are my least favorite form of entertainment, but it was my way of showing her that I could make a fool of myself after she accused me of being too serious. I am a serious guy, and I definitely wouldn’t do show tunes for just any woman.”

— Drew, 29


12. “I spent $500 on the perfect date because I wanted this girl in college that badly. First, drinks at a ridiculously expensive rooftop lounge overlooking the city, then dinner at a fancy restaurant (I didn’t even like the food), where I tipped the violinist to play a special song for her, and then I hired a rickshaw to get us back to campus. It was a solid night, and we ended up having sex. What I didn’t expect was that the whole thing would transform my reputation and that literally every single girl would start looking at me differently. I became the school Romeo—until I made the mistake of getting caught cheating.”

— Martin, 26


13. “In middle school, I changed my entire look overnight after I overheard my crush say that she liked guys who wore all back. It was so pathetic. I hate black but I wore all black for two straight weeks just to get her to pay attention to me. When she started going out with this preppy jock, I realized I was wasting my time.”

— Colton, 22 TC mark

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