The worst part of dating? Being rejected, of course! From embarrassing love letters to pathetic pranks, these daters recall the time they were brutally rejected by their crush. Content has been edited for clarity.
“I Was Completely Shocked And Mortified”
“Let me preface this by saying that I’m a guy.
This incident happened in middle school during the last few days of eighth grade. Afterward, I went off to high school. I didn’t know much, but I knew I had a crush on someone I had known since fifth grade.
After a few tormenting days, I finally got the courage to write the most intricate, most delicate love letter I had probably ever written. It wasn’t creepy, it was more along the lin‘I really like you, and I know it’s weird for a boy to say that to another boy. But it’s the end of the year, and why not.’
At the very least, I would know I tried instead of wondering about what could have happened between us. So, I gave the letter to him and asked him out.
I told him, ‘The letter is kind of personal. Can you wait to open it until you get home?’
He nodded and took the note home. Tomorrow would be the day.
I couldn’t have been more stressed. I couldn’t eat, and I certainly couldn’t sleep. My heart raced the entire night while I lay in bed. Finally, the last day of school arrived, and I sat on the stairs reading a book and waiting for the morning bell to ring. I was in the lobby, so the entire student body was crowded around waiting for the bell to ring so we could scatter to our home rooms.
Right there, loudly, in front of everyone, the boy I liked took something I wrote personally and made it into a public spectacle. I was shut down in front of the entire middle school, and at the same time, outed. I was completely shocked and mortified. He didn’t even do it nicely, let alone privately! Until this point, he was the nicest guy I had ever known.
I didn’t cry. I didn’t think I could have cried with everyone standing around me silently, watching me like they were. When the bell finally broke the silence, everyone shuffled off to class.
The next year, in high school, his friend was in my English class. I didn’t know why or how we started arguing, but the friend started reciting something familiar.
It was excerpted from the love letter I wrote. The boy I had a crush on and worked up the courage of a thousand suns to ask out showed all of his friends.
I was mortified. Luckily, I later realized what love really was.”
“I Had Never Been So Humiliated”
“This happened in high school during my awkward phase.
One time, my mother told me I looked pretty. In turn, I worked up the courage to ask out the cutest guy at my school to the movies.
After I asked the guy, he replied, ‘I’ll have to think about it,’ and took my phone number. I was excited, and I thought it was a good sign.
We texted back and forth a few times and arranged to meet up at the movie theatre. When the day arrived, I took my time getting ready and did my hair and makeup perfectly. I thought I looked gorgeous.
When I got to the theatre, I saw him standing in the lobby.
But all of his friends were there, too.
All of his friends, including the guy I liked, were laughing at the absurdity of how he could ever want to go out with me and laughed at the fact I got dressed up for nothing. It was all a big prank. I had never been so humiliated in my life.
Eventually, I got over what happened. I thought it made me a nicer, more sensitive person when approaching new relationships. Afterward, I always tried to look past people’s appearances and look for who they were on the inside. It was probably beneficial in the long run.
As for the guy, he went bald and peaked in high school.”
“She Rejected Me In The Most Embarrassing Way Possible”
“When I was twenty years old, I worked up the courage to ask out a very pretty, smart, funny, and seemingly down-to-earth girl in my social circle. During this time in my life, I was constantly ‘friend-zoned.’ I had even asked a girl out on a date more than once, and the girl didn’t realize it was a date. I kept thinking I was getting close to girls, but then they would suddenly start dating my brother or one of my close friends.
This time, I said straight out, ‘To be clear, I’m asking you on a date.’
The girl laughed and accepted. I was psyched!
Then, I started getting phone calls. Several phone calls from other friends, one after the next. This was before the era of texts, of course. The girl I asked out had called multiple friends and acquaintances, telling them about how I asked her out, how she didn’t want to go, and how she wanted their advice for ‘letting me down gently.’
I was mortified. Now, not only did I not get the possible date I had spent weeks working up the courage to ask out, but she rejected me in the most public and embarrassing way possible. I left this friend circle shortly thereafter. The girl calling my entire social circle to explain how she was rejecting me so she didn’t have to do it herself was about as bad as it got.
I didn’t learn how to ever be a player, though it has a happy ending. My wife of twelve years and I still disagree on when we started dating. She claimed we were just hanging out as friends for a month before we went out, but I thought we were dating the entire time.
Oh well, it worked out okay.”
Problematic Prom Date
“Before my twelfth-grade prom, I finally worked up the nerve to ask the girl out who I had been dreaming about for the last four years. To my astonishment, she said yes! Sadly, however, her family couldn’t afford to purchase her a dress for prom. So, I promptly offered to buy a prom dress for her.
My date appeared to be very happy, and after some time, she asked, ‘Do you think we should get a hotel room for prom? We can go early, book the room, then go home and change.’
I thought it was a great idea, so we booked the room first thing in the morning on the day of prom.
My date grabbed the room key when the clerk handed it to us, smiled, and said, ‘Okay, I’ll see you tonight!’
We had already planned our limo and paid for it. I found it odd how my date wanted the limo to pick her up first, but I tried to shrug it off. She claimed she wanted to meet my parents, so I agreed. I went home, got ready, and waited for her to arrive.
An hour passed, and the limo never arrived. My date wasn’t answering her phone.
I got in contact with my buddy who was already at prom and he explained, ‘Man, she’s already here with some other guy. It looks like she is wearing the dress you bought her, and they took the limo here.’
My date and the other guy took the hotel room I paid for, too. Needless to say, I have trust issues to this day.”