When Rejection Stings: 50 Brutal Dating Comebacks That Went Too Far
Ever wondered if there’s a “right” way to get dumped? Spoiler alert: there absolutely isn’t. Sometimes that dreaded “no” comes wrapped in a punchline, a cold shoulder, or even a desperate plea disguised as a date invitation. Imagine being asked out only for the other person to admit, “I’m only asking you because I’m desperate.” Talk about a confidence crusher masquerading as honesty! These stories dig deep into the hilariously awkward, painfully awkward, and downright brutal moments when rejection served more than just a simple “no”—it came with all the extra emotional baggage you didn’t ask for. So, buckle up, and prepare to cringe, chuckle, and reflect on those moments when love’s rejection stings a little more than expected. Because let’s face it: sometimes the worst thing isn’t the rejection itself, but how it’s delivered. LEARN MORE
I think this might make it worse, but it actually occurred when she was asking me out.
She said “I’m only asking you because I’m desperate”
DrGeraldBaskums:
Nice how’d the date go?
OP:
It was awkward. We watched Horton Hears a Who and shared Raisinettes, and she asked me halfway through if she could hold my hand. I was like sure.
We didn’t go on a second date.
helen269:
Sounds like someone who has never been approached, has never been chatted up, has never been asked out on a date, and was “desperate” to know what it was like.
When I was in like 8th grade we had a dance. I spent like an hour hyping myself up to ask this girl for a dance. I walked up to a group of the girls and ask her and she just kneed me in the nuts. No words and just that.
I never did figure out what the hell that was about.
SgtDoakes123:
Ah yes memory unlocked. Was 16 or 17 at a bonfire kinda outdoors party/gathering. Saw a cute girl standing with two friends whom I’d never seen before so I decided to go over and talk to her. I was gonna say something like “Excuse me do you know where people are getting drinks” or some super smooth thing like that.
I got to “Excu..” before she punched me in the stomach and I doubled over on the ground gasping for air. Took me a minute or two to recover and when I got back up they were gone so didn’t even get to curse them out. Good times.
It was Halloween, and I was at a bar. There were 2 girls who were clearly besties, and they were very aware that they were the hottest girls at the bar. They were each wearing typical hot girls Halloween costumes. Think ‘devil costume’ consisting of a red dress and plastic devil horns. I don’t remember what their exact costumes were, but I went up to one of them and said “Hey, you look like a cute [whatever her costume was]”
She responded with “You look like a loser.”
They both laughed and walked away.
I laugh now when I think about it, and the story always gets a rise when I tell it. But at the time, I felt like a loser.
unreall_23:
How people can be so intentionally cruel. In my life, I can honestly say that i haven’t purposely put someone down.
Wrenchheader:
Immature minds don’t care.
I wrote her a note asking her out, she wrote ‘Ew’ on it and sent it back.
Chillow_Ufgreat:
She sent me the note, with the “will you go out with me yes/no” boxes to check. Even wrote “Serious – not a joke!” at the bottom. So I checked yes and sent it back.
So imagine my reaction to discovering that it was, in fact, a joke.
We were in high school, I sat next to her and we started talking, everything was going great so I asked if she wanted to go see a movie.
She looked around and then said “Look, I don’t want to be mean so just tell people we found out we’re cousins.” Then it was awkward for a few seconds until she switched seats.
I can still smell the room we were in because of how bad that memory is burned in my brain – ouch Patricia, not cool.
Disastrous-Score-213:
Similar situation. In high school I would ride the bus with a girl who was a distant cousin. We both knew we were related, and I assumed she was aware that she was not a love interest. My other, closer cousin and I were going to a movie, and I asked if she’d like to go, too, thinking that I was asking a cousin to accompany two other cousins to a movie in order to watch a movie. She must have thought I was asking her on a date, because she said “aren’t we related?” Me, having no idea why that would matter when going to a movie with family, said “So?” I was in utter confusion because I was already going to the movies with my cousin, and she was my cousin, so why wouldn’t another cousin go to a movie just because we are related? Took years to realize that she thought I was asking her on a date, and then I realized she thought I didn’t care about dating a relative after my response. I still cringe thinking about it.
This wasn’t on her, but I still think about how awkward it was and how I wanted to die.
The setup to this was I thought I had a secret admirer in my junior year of high school. I received a couple notes from an unidentified girl, nothing over the top but just enough to seem legit saying she thought I was cute and asking if I had a girlfriend. This was early 90’s so no social media, texting ect.
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