Skip to content
Search AI Powered

Latest Stories

Guys Describe The Worst Dating Rejection They Ever Experienced

two people's hands holding ceramic mugs with coffee on wooden table
two person holding ceramic mugs with coffee

Single men who are ready to leave their bachelor lives behind and pursue relationships may have one obstacle they're not quite ready to face—rejection.

We often fantasize about dating the person we have a crush on only to have reality slap us in the face after realizing the object of our affections doesn't share the same gushy feelings.

That prohibits most of us from having the courage to ask someone out. Some people's egos are way too fragile.

So how do you encourage someone to throw caution to the wind and take a chance on love? Just tell them to go for it. Besides, what's the worst that can happen?

Apparently, it turns out there are some worst-case scenarios as experienced by these single cisgender males who were turned down and drop-kicked to the curb after asking a girl out.


Curious to hear about their shattered self-esteem, Redditor JadenYuki15 asked:

"Dear boys of Reddit, we all know the whole, 'the worst thing she can say is no,' and that its bs. What's the worst rejection you've ever received?"

Stingers

The zingers here really dented these Redditors' self-esteem.

Harsh Dis

"I asked a girl out in high school and she just looked at her friends, said eww, and walked away. It crushed my self esteem for months."

RedBeardedTallGuy

A Horrible Person

"There was this girl I was on good terms with. Good friends for a number of years, always had a crush on her but just decided I was done hiding that. So I asked her out."

"You'd do much better asking a face surgeon for a consultation. I'm going to take a shower. Bye."

"Yeah...I mean, we were good friends, a simple 'no' would have sufficed. Unsurprisingly our friendship didn't last much longer because boy oh boy she turned into a horrible person. And by that I mean she started hanging with some really f'ked up people, and when I did actually end up in a relationship, she got super jealous (the f'k) and tried her best to end it. And she succeeded."

We1tfunk

The Punchline

"At a bar with a friend, I asked a girl for her number and she said, 'I have one but not for you.' I went back to my friend and we laughed and got drunk."

akamustacherides

The Bad Insult

"I asked someone out and she said she'd pardon my language: never go out with a 'retard.' I have borderline intellectual functioning but she called me that because I was in special Ed classes. Here I am at 27 and haven't asked anyone out since high school."

wastedplacidity

Mr. Cellophane

"I'm sorry. I don't date people that don't exist."

homevp

Awkward Red-Faced GIF by moodmanGiphy

Salt On The Wound

In addition to being rejected, more humiliation was to come for these poor guys.

Sorry, J.K.

"I went to school with a girl I ended up nicknaming JK."

"Her initials were actually JK, so she never thought much about it, but I called her that because she was always 'just kidding'."

"She would flirt with you nonstop, making you think she really had a thing for you, until you built up the courage to ask her out. Then she'd laugh and say she didn't think about you like that."

"Weeks later she'd start flirting again, really pouring it on that she wanted you, rinse and repeat."

"Wasn't 'the worst' rejection or anything but man was it aggravating to keep falling for it!"

MaestroLogical

The Popular Girl

"I asked a girl out privately in highschool, she rejected me politely but told everyone at school that I asked her out. That would have been fine but she is a popular girl in highschool while I am an ordinary, unnoticeable student. Every boys that liked her bullied me until the end of the year for confessing to her."

dubu_dubu22

Former Flat Earthers Explain What Finally Made Them Come Around | George Takei’s Oh Myyy

Science is science. Fact is fact. Truth is truth and simple is simple. These are things we must now attest to in 2021. Can we please all get onboard with wha...

Team Effort

"Making small talk at a bar with a girl and offered to buy her a drink. She said 'nooo, I'll buy you a drink!' Can't argue with that, I thought, and accepted."

"She got me a gutter shot... Apparently she was dating the bartender and it was a thing they did whenever she got hit on."

"Ninja edit: a gutter shot is when the bartender scoops up a shot glass full of whatever spilled drinks ended up in the trough behind the bar. It's disgusting and probably not sanitary. Anyway, she was a b*tch and that bartender was an a**hole. I left without paying and never went back."

KilgorrreTrout

Twisting The Knife

"I told a girl in high school i had feelings for her and then she completely ignored it and told me about how she was f'king her personal trainer and proceeded to send me pictures of them together."

Admirable_Surround_7

Height Prejudice

"She laughed in my face and said, 'Oh, you were serious? I don't date short guys.' I'm 5'4."

"6 years later I'm doing very well, she is couch-surfing."

"Saw her at a bar recently and she didn't recognize me, partly because I grew a beard and partly because she was so sloshed."

"She tried to hit on me, and I'm actually proud that I just said no thanks, but I'm flattered."

"Proud of myself, sad for her."

DeelBreaker

Scorned Dance Partner

"Girl I was in to in middle school, who was supposedly into me to. We used to dance at the dances, kind of. At the end of one, everyone was pairing up for the next dance, so I asked her if she wanted to go to the next dance with me. No hesitating, she just said no. Hurt like hell. But I still had feelings for her and it ruined a possible relationship later because I couldn't let that girl go."

whyisreplicainmyname

The Shallow Date

"A friend set me up on a date with a wonderful woman and we got along well. But when I took off my hat and revealed that I was bald, she gasped and walked briskly to the bathroom."

sd_glokta

Lies

The passive aggressive type of rejection cuts deeper.

The Excuse

"I met this girl at a Metal concert (specifically Gwar), she came up to me and was scared because of the mosh pit, and insisted I hold onto her because I was the biggest guy there (6'5" and 250lbs), she was cute so of course I did. After the show ended I forgot to get her number but gave her a drumstick of one of the opening bands. Fast forward a few days later I get a message on Facebook asking if I was the guy who gave her the drum stick, and I said yes. We ended up hanging out, a few times, got lunch, and I asked her out, I was told she does not date younger guys (she I guess was 25, I was 20 at the time), Fast forward a few days later, I find out she was dating an 18 year old so surprised me with a curveball."

Ghoulthrower676

Presumed Single

"I bought a girl a few drinks at a nightclub in my early twenties. After about 3 drinks, I asked her if she wanted to come hang with my friends and I. She leaned in and gave me a kiss on the cheek and says 'Thanks for the drinks I have to get back to my boyfriend now.' My guy friends were laughing their a**es off."

RAM_592

The Prom Date

"Asked a girl to our prom in high school. She said someone already asked her. She came with her brother."

Nathaniel66

Based on these responses, it seems some rejections are no worse than any of the others.

Although it may still sting, "I'm just not that into you" is better than a cruel punchline harsh enough to annihilate a dude's self-esteem, stomp it to pieces, and pour acid all over it.

The good news is, the ones who have the capacity to insult you at a vulnerable moment are the ones you would not want to take home and introduce to mom.

Don't give up hope, gents. There's definitely a keeper out there somewhere for you who will be worth the wait.


More from Trending/best-of-reddit

Miriam Margolyes
David Levenson/Getty Images

'Harry Potter' Star Miriam Margolyes Offers Mic Drop Explanation For Why Respecting Pronouns Matters

Sometimes it is just that easy to make people happy. This is a lesson learned over and over in our lives, but that's because it's an important one.

Actor Miriam Margolyes shared how she learned to change her behavior to make others happier. Margolyes appeared on The Graham Norton Show recently and brought up a fairly polarizing subject in the United Kingdom: trans people.

Keep ReadingShow less
Elon Musk looks on during a public appearance, as the billionaire once again turns a newsroom style decision into a culture-war grievance broadcast to millions on X.
BRENDAN SMIALOWSKI/AFP via Getty Images

Elon Musk Cries Racism After Associated Press Explains Why They Capitalize 'Black' But Not 'White'

Elon Musk has spent the year picking fights, from health research funding to imagined productivity crises among federal workers and whether DOGE accomplished anything at all besides leaving chaos in its wake.

His latest grievance, however, is thinly disguised as grammatical. Specifically, he is once again furious that the Associated Press (AP) capitalizes “Black” while keeping “white” lowercase.

Keep ReadingShow less
Elon Musk; Yale University School of Engineering and Applied Science
Brendan Smialowski/AFP via Getty Images; Plexi Images/GHI/UCG/Universal Images Group via Getty Images

Elon Musk Gets Brutal Wakeup Call After Claiming That Yale's Lack Of Republican Faculty Is 'Outrageous Bigotry'

Elon Musk—who has repeatedly whined about diversity, equity, and inclusion (DEI)—took to his social media platform to whine about a lack of conservative faculty at Yale University.

Musk shared data compiled by The Buckley Institute (TBI), a conservative-leaning organization founded at Yale in 2010. TBI found 82.3% of faculty self-identified as Democrats or primarily supporting Democratic candidates, 15% identified as independents, while only 2.3% identified as Republicans.

Keep ReadingShow less
Barry Manilow
Mat Hayward/Getty Images

Barry Manilow Speaks Out After Postponing Farewell Tour Dates Due To Lung Cancer Scare

"Looks Like We Made It" singer Barry Manilow is in the process of saying goodbye to the stage and meeting his fans in-person, but he has to press pause for a few months after receiving a jarring diagnosis.

On December 22, 2025, the "Mandy" singer posted on Facebook, explaining that a "cancerous spot" had been discovered on his left lung.

Keep ReadingShow less
Chris Evans as Steve Rogers in Avengers: Endgame, the last time audiences saw Captain America before his unexpected return was teased for Avengers: Doomsday.
Disney/Marvel Studios

Marvel Just Confirmed That Chris Evans Is Returning For 'Avengers: Doomsday'—And Fans Have Mixed Feelings

Folks, once again, continuity is more of a suggestion than a rule in the Marvel Cinematic Universe. Marvel has officially confirmed that Chris Evans is returning as Steve Rogers in Avengers: Doomsday, and the internet has responded exactly how you’d expect: screaming, celebrating, arguing, and a very justified side-eye toward how Sam Wilson keeps getting treated.

The confirmation comes via a teaser now playing exclusively in theaters ahead of Avatar: Fire and Ash. There is no official online release, despite leaks circulating. If you didn’t catch it on the big screen, Marvel’s response is essentially: sorry, guess you had to be there.

Keep ReadingShow less