Heartbroken People Share Their Worst Rejection Stories

June 26, 2023 | Carl Wyndham

Heartbroken People Share Their Worst Rejection Stories

We all know it takes a lot of courage to ask someone out on a date. Now, we can understand why.

Not every unsuccessful request to spend quality time with someone is met with politeness and understanding. In fact, at times it can be met with precisely the opposite. There is no limit to the lengths some people will go to in making sure that someone is rejected without any shred of sympathy, dignity, or shadow of a doubt as to how the object of their interest feels—whether the person deserved it or not.

Here are 41 of the most painful, weird, and wild stories of rejection from the world of dating, and beyond.

1. Merry Christmas!

My worst rejection? My girlfriend dumped me two days before Xmas. Little did she know, my gift was going to be an engagement ring…


2. Inside Job?

I fancied this guy for ages, and my friend convinced me to ask him out. So I did, and he said no, as I expected. The next day, my friend asked him out and he said yeah. They only broke up last month, about four years later. So not only did I get rejected, but I had to watch my friend and him be a couple, which hurt for the first while.

Woman at party rolling eyes at affectionate couple.

3. Very Bizarre...

I don't fault people for their romantic preference at all, but there was this one girl I met online who just ticked me off when we met in person. We had chatted for a week beforehand, traded several pics, etc. She gave off a couple of really weird red flags during our hour-long coffee date, but I thought it was actually going really well until she abruptly ended it. "Look, I'm sorry, you're a nice guy, but I don't think this is going to work out. I just don't find you attractive. I really just don't like Asians". What the heck? Aside from the racism there, you knew I was Asian going in, so why bother wasting my time?

Handsome Malaysian Man.

4. The Wrong Kind of Love

I was friends with this girl who was a grade above me in high school. We were friends on Facebook, and one day she decided to list me as her brother…

High Angle View Of 'Family' Text On Cake.

5. Dining and Diving

Met up with a girl from an online dating site. We sat down at a restaurant and grabbed the first round of drinks. So far, so good. Decent conversation ten minutes in. She then asks if she can excuse herself a second while she goes to the bathroom. No problem. She walks away and two minutes later, the waitress comes over with the check. I gave her a confused look.

The waitress says that she thought we were leaving, because my date just walked out the front door and got in her car. Sure enough, ten minutes in was all this woman needed to decide to just back out, and not even have the human decency to finish her drink and just run away.

Never even bothered to text her to ask what was up. Finished her drink and then headed back home.

Portrait of man drinking beer in pub.

6. Plot Twist

I told my ex-boyfriend I wanted to end things, and he basically said, "lol no". He rejected my breakup. That was weird...


7. NOT!!!

I had someone come up to me and say they liked me. I smiled, then they said "Hahaha, just kidding. You're a loser".

These things sting for months, man.

Businessman making fun of you reaction.

8. You’ve Been Had

My "worst" was in the sense that she was just using me the whole time. Met at work, hit it off, talked daily and would always go out together on lunch breaks. Little did I know, she'd purposely "forgotten" her wallet. So basically, I was used for food all the time. And any time I'd ask her to go out on the weekend, she'd make up some excuse.

Took me a little while to catch on…

Customers paying waiter at restaurant.

9. Blindsided

I was on a blind date. Date was going well. On her way to the restroom, she met another guy and snuck out the back with him. The bartender saw everything, and gave me free drinks for the night. At least I had that, I guess…

Young man holding head looking at receipts.

10. Who Did I Reject Again?

I was going through a real tough spot emotionally after my wife left me. After a few weeks of pouting alone in my apartment, I got talked into going out to a dance club with some friends. One of my friends found this group of girls who were all pretty, and we danced together until we closed the place down. There was one girl that I liked in particular, and she seemed to like me too. We danced a lot. Even when the DJ played a slow dance song. After we left, I asked if we could see each other again and she said, "Sure! I bowl every Wednesday night at the bowling alley". We had talked earlier and had a love of bowling in common, so this was great. I told her I'd meet her there at 7 pm and we went our separate ways.

Wednesday night I get to the bowling alley and she's on a lane with like four other girls and two guys. I walk over with my bowling ball bag and stand near her until she makes eye contact, and when she does it conveys a look of who the heck are you?

The evening did not go as planned...

Young girl posing with her palms up.

11. The Truth Comes Out

Well, I guess I was the one doing the rejecting here...

When I was in college, I was a bit of a nerd magnet. I have a permanent friendly face, so to most of my fellow physics classmates, it came off as flirting. Needless to say, there were multiple occasions when my geeky lab partners would ask me out and I would politely decline.

Unfortunately, at the end of the semester, our professor made us work on a 6-hour lab outside of class. My lab partner was a snack pack version of Jason Mraz, and he asked for my number so we could set a lab schedule. After multiple texts asking me out, sending me good morning and good night texts, I stopped responding—until one day he called me.

I was on a date with a boy and tried to hit ignore before my date noticed. My date asked what was going on and, in so few words, I told him that my lab partner is obsessed with me, I didn't want to be partners with him, that he was gross and annoying, and that he was one of the most repulsive people I had ever met. My date and I laughed, but as I looked down at my phone, I saw that the call from my lab partner had been answered, and that he had been listening the whole time...

12. Cross My Heart and Hope to Die

I had a girl actually fake her own suicide once because I asked her out. True story.

Crazy shocked young man, looking at camera with wide opened mouth.

13. Throwing Her Under the Bus

I had a crush on a guy for years when I was a teenager. My friend begged and begged me to tell her who I liked at our graduation party. She promised she wouldn't say anything. As soon as I told her, she was like "I'm going to tell him," then ran off to do so. I ran and hid behind a pillar. It turned out he did not feel the same way. He found me at the end of the party and just gave me a hug. At least he was nice about it, but man, that was so not cool of my friend.


14. Double Whammy

I was at a party in high school and I made a move on my crush at the time. She turned me down quickly, and that was that...until the next school day. She apparently went around telling everyone that we hooked up, but that I had a tiny you-know-what and I had trouble getting it up.

She not only refused my request, but assured no one at the high school would ever think about getting with me again.

Students gossiping in school hallway.

15. Way to Go Back on a Promise

I had a crush on a girl at my church from 7th grade until like 11th. We’ll call her "K". I altar-served with her younger brothers, our moms were friends, and my whole family knew I was bonkers over her. No one outside the family did, though. Eventually, my best friend spends the night and next thing I know, I'm telling him about my crush on K, after swearing him to absolute secrecy. Like, I-would-find-him-and-cut-him-to-bits-if-he-told-anyone secrecy. I was reluctant because he knew who she was (but not enough talk to her).

My worst fear came true. After church THE NEXT SUNDAY, he was adamant that I had to go tell her how I felt. Of course, I would have rather died. He joked (I THOUGHT) that he was going to tell her if I didn't. The jerk did. In front of my family, too. I wasn't there. From what I was told of the conversation:

Him: "Blank likes you".

K: "Oh... I like him too".

Him: "NO, he REALLY likes you".

K: Oh, well I like him, but just as a friend".

She was so nice about it, but I never spoke to her again.

Words Love And Friendzone In Missing Puzzle Piece.

16. I Didn’t Catch Your Name...

In a club once, my friend had been talking to some girls. He came over after a while and introduced me to them. He got as far as "this is—" before the girl looked at my friend, shook her head, and turned around. Ice cold.

Teenage boy surrounded by group of people dancing at party.

17. Wingwoman

I was talking to a girl who was out with her friends. Partway through, one of her friends chimed in and was like, "Why are you still talking to her? Look at her and look at yourself. Do you really think she'd be interested in you?" The girl I was talking with just laughed at how mean her friend was being to me.

Good times.

Teenage boy looking at couple in love.

18. Fair Weather Friends

At a high school dance, I decided to organize a little get-together with some friends of mine and of the girl I was taking to the dance. Had numerous people say they were going to come by and thought everything was solid.

After dinner and the dance, she said she wasn't feeling well and I took her home.

I went home to prepare for the guests because I figured this would still be an OK evening.

Not a single person showed up.

I found out later that the girl had actually wanted to go do something else afterward with another guy, and everyone else just had something better to do.

I felt like I was rejected by the girl and numerous friends, and it felt like a gut punch.

Cropped image of sad break up.

19. Bookworm

By far the worst was at a bookstore once. I was there and saw this really cute girl browsing through a book that I'd read before. We'd made eye contact a couple of times earlier, which I apparently totally misread. Earlier that day, I'd seen one of those popular images that go around, where a girl says, "Just once I'd like a guy to offer to buy me a book instead of a drink". So I thought I'd try it. I go up to her, say something like "That's a fantastic book. You have very good taste. Mind if I buy you a book?" I don't remember her exact response, but "go away" and a nasty slur were both in it.

Talk to hand reaction.

20. That Escalated Quickly

A guy, trying to find an excuse to initiate a conversation with me, asked me to open the window that I was sitting by on the bus because he was hot. I said no, I wanted to keep it shut. I didn't like having it open because my hair always flies out the window. He looked at me, said "whatever, you're ugly anyway," and reached over and opened my window.

Thoughtful woman sitting in a bus.

21. I Feel a Water Park Coming to My Eyes After Reading This

Went on a double date of sorts with my friend. We went to a water park. So an entire day was spent with my friend (who is quite attractive), two quite attractive women, and me (who is a solid 5/10 on a good day). We did water slides, wave pool, the works. It was a nice day and I didn't even get sunburned.

Two days later, I decided to ask out the girl who was my date on a solo date. She. Did. Not. Remember. Who. I. Was.

It wasn't that she said I wasn't attractive. It's that she spent an entire day with me and paid so little attention to me and what I looked like that when I saw her next she did not know that I was the same guy who she spent 8+ hours with less than 48 hours ago. She must have never looked at me the whole day.

Teenage girl gesturing with palms up.

22. Living a Lie

In third grade, I wasn't very popular. I was the skinny white kid who wore what his mother made him wear and had no confidence. The bullies were real.

I had two girls in my class suddenly come up to me one day, link arms with me on each side, and tell me how "cute" I was and how they both wanted to be my girlfriend. This went on for days. I was so happy and surprised that any girl liked me, let alone two. We would go to recess together, eat lunch, talk about our day—it was great. I vividly remember both of them mentioning wanting to have intercourse with me once.

All of this came crashing down, though, when the girls’ original boyfriend announced to them that their work was done, and everyone proceeded to laugh at me while they left and went off with him. He had set me up with them just for this moment of humiliation. The girls took turns saying things like, "You think any of us would like you?"

Looking back, it was very traumatizing and I'm surprised this occurred at such a young age. It wasn't until I was a junior in high school that I actually gained some confidence and self-worth.

Depressed man sitting head in hands on the staircase.

23. Life Changes in an Instant

For seven years, I was always in love with my best friend.

Eventually, I decided that I had to tell her—and her reaction was to tell me that she didn't want to be part of my life anymore. At all.


24. No Contest

Friend wanted to meet a guy she had met on the internet, and asked me to come along because she was nervous. On the way there, she told me she brought me along instead of our other friend, "because with her I would have to worry about him thinking she is hotter than me. I don't have to worry about that with you".

Young women talking and laughing in courtyard of hostel.

25. Oh, Snap!

Back in college, which was longer ago than I care to admit, I was backpacking through Sweden with a friend. He was quite enthralled with Swedish women and constantly trying to hit on them. One day, he asked one: "Excuse me, do you speak English?" and she answered "Not today" and kept walking.

'Talk to the hand' reaction.

26. Layers of Strength

One guy once refused to go out with me because he said I looked like a human Shrek. I said, "Thank you, sir—Shrek is gorgeous!" I then went home and cried a little…

Madame Tussauds Wax Sculpture Museum in Istanbul.

27. Vanished Into Thin Air

Got dumped by the girl I was going to propose to in a foreign city, halfway through a two-week vacation. She just disappeared on me. I knew something was up when her luggage disappeared from our hotel room. She ignored every text I sent her, and I didn't hear from her for six months until she finally sent me a message: "How are you doing?"

I guess she got concerned—or as concerned as a heartless reptile can be—when I stopped updating Facebook and Instagram, and changed all my statuses. She never got a response from me, and went on permanent block. She then tried to blow up my Facebook, until I unfriended her. I may have talked to her had she provided an explanation, but she never did. Screw her.

Japanese macaque giving the finger.

28. What Does That Even Mean?

Someone I liked said my face looks like an acne pizza. It made me cry!

Headshot of disgusted girl.

29. Rejecting Many Along With Me

I had a girl who said that she didn't see men of my ethnicity as real men. She then tried to play it off as a joke after she realized how ridiculous that statement is. Jerk…

'WTF is happening!' reaction.

30. But Tell Us What You Really Think

He looked me up and down, said "Pass," and then walked away.

Young blond woman raising her hand.

31. No Light at the End of the Train Tunnel

When I was a teenager, there was this amazing girl in our circle of friends who I was really attracted to. She was really cute, funny, and great fun to hang out with. Nothing happened at the time because I assumed the feelings weren't mutual, and I'm oblivious to any flirtation anyway.

When I was about 17 or 18, I moved away to a different part of the country with my family. That girl and I slowly stopped staying in touch, and I began to think about her less and less. That is until one morning about a year later, I woke up to a message from her on MySpace, explaining that she'd always had feelings for me but hadn't said anything at the time because she assumed the feelings weren't mutual. She wasn't expecting anything to come of it but just wanted me to know.

I couldn't believe it. I'd never had anyone express interest in me like that before. For it to be coming from her was like a fairytale or something. So I messaged her back saying I felt the same and we chatted for a little bit. We were both giddy with excitement. All the while I was thinking about all the great times we'd had together and how much fun I always had when I was around her, and eventually I just thought "screw it," I'm not going to ignore this. So I told her I could come and visit. Today. Like, now. I was so excited to see her again and she felt the same.

Train tickets were going to be expensive and I was skint at the time, but I'd have emptied my savings to see her again. So I packed some overnight stuff, told my mom I was going to stay with a friend, took the next train to the coast and arranged to meet with her. I decided I'd just find somewhere to stay while I was there, whatever. She explained she was seeing friends later that evening but we could spend the afternoon together just the two of us, and then I could join her in the evening to hang out with her friends and I could stay at her place.

So that's what we did. Mostly anyway. It was a hot sunny day, so we spent the afternoon just lying around in the cathedral gardens, catching up, reminiscing and talking like we used to. At some point, we went and met her friends. I got to know them a bit, just hanging out, making the most of the summer evening, drinking beers as night fell. She got introduced to some new people who were friends of her friends and she got to know them a bit too.

In particular, there was this one dude who seemed more interested in getting to know her than he did me. I didn't think much of it though, even when she disappeared from the group for a while and I noticed he wasn't there either. Eventually, though, I decided I'd better go and see where she was, as I was meant to be staying at her place and it was pretty late by this point.

I found them. They were making out like they were the last people left on the planet. She was pushed up against a wall with her legs wrapped around him. She clocked me, stared at me, and just said "Sorry". And that was the last time we spoke. I stayed in the spare bedroom of some friend of hers who I barely knew, tried to pretend like it was all cool, and got the train back home the next day.

Young Man Traveling In Train.

32. Different Goals

My sister hooked up with a classmate a few times and said they got along very well, sometimes coming over to hook up and never getting the chance because they would get so lost in conversation.

So one day she goes, "Hey, we get along well and I think you're pretty attractive, maybe we can go on an actual date sometime?"

Without a beat, the guy looks to her and says, "Listen, I'll sleep with you, but I can't be seen in public with you".

She claims she clocked the guy and never spoke to him again.

Young couple having argument at home.

33. Preventative Measures

A co-worker came up to me and told me not to even think of asking her out. Umm, I wasn't going to—but thanks for randomly telling me how much I apparently SUCK.

Two colleagues talking in office.

34. Rejected by...Myself?

I had low self-esteem in early high school, so one day at lunch I was like, "I'm going to ask the first OK-looking girl who comes around that corner out and they'll say no". So, the first person to walk around the corner is a pretty girl. I ask her out and without hesitation, she says "sure".

Now, I was 100% expecting to be shot down, so I caught myself unprepared. I kind of stuttered "Haha just kidding," then walked away and face-palmed. In short, some girl got asked out, said yes, only for the guy (me) to awkwardly say, "Haha just kidding" and walk away. I shot myself in the foot hard, and it still haunts me…

A young man in a denim shirt closing his eyes with his hand.

35. The Coming Attractions

Me and my best guy friend at the time were planning on going to the movies to see Deadpool last year. We lived on different sides of campus, so we planned on meeting at the theater. I thought this was going to be like a date, so we split a popcorn and grabbed seats.

We chatted a bit, and once the previews started, he leaned in towards me and I definitely thought he was going in for a kiss. I went for it, only to be met by his hand on my mouth pushing me away and a weirded out look on his face. Turns out he was trying to ask me to move down a seat because he had decided to invite his new girlfriend (who I had never met or heard about) and he wanted to sit by her. Not only was I mortified, but he kept the popcorn for himself and this chick. First and last time I initiate plans.

Smiling couple ignoring friend.

36. At Least You Could Still Get Dinner…

I was once given the number to a pizza place instead of the guy's number I had asked out.

Vector pizza illustration with slices and many ingredients.

37. The Perfect Moment, At Last!

I'd been toying with the idea of pursuing a relationship with a cute, girl-next-door kind of person just after high school. We had known each other through high school, but only really connected as friends about a year after we'd graduated, over summer vacation when I'd come back to my parents’ house for the summer.

I felt like she was into me too, and we went on a couple of us-only dates, so I was fairly certain I had a shot. One night after hanging out with a bunch of other people, most everyone had gone home and we were hanging out for a little bit after. We'd walked to a nearby gas station to get something to drink and had made it all the way back to her driveway. It was like 3 in the morning, so I wanted to go home and sleep, but I had one more thing to do before I left. It was a clear night, cool but not cold, and there was no moon, so you could see more of the sky than usual. It was pretty much as romantic an opportunity as it was ever gonna get.

We were hugging goodbye, and the hug lasted a little longer than normal, and when she pulled away she looked up at me and smiled. I tried to seize the moment in the stupidest way possible—I said "Can I kiss you?"

Her eyes went wide and she blushed but didn't answer. She just hugged me again and buried her face in my chest. I wrapped my arms back around her and just kind of patted her on the back. I heard what sounded like muffled sniffles coming from her and I hugged her tighter, "It's ok, don't cry".

I soon realized she hadn't been crying. She'd been laughing.

Teenage girl hugging her father.

38. Seems a Little Harsh...

When I was eight, I was on a road trip with my family, and my dad got lost. He got REALLY angry when he got lost. So to vent his frustration, he pulled over to a Jack in the Box and had me come in with him (he demanded that only I come with him, no one else). He relieved his tensions by sitting me down and telling me for ten minutes why he didn't like me.

From the way I cleaned my room, to the way I did in school, to the way I SPOKE—he told me how he despised everything about eight-year-old me. I'll never forget him saying, "I don't like a single darn thing about you". Hard to take when you're eight and your dad is still Superman to you.

Father disciplining his daughter.

39. Santa’s Been Naughty

I got rejected when I wasn't even trying to hit on the guy. A few years ago in December, I was at a bar with a friend when a guy dressed as Santa Claus was walking around. He walked up to my friend and said something like, "Santa's giving out gifts, and all the pretty girls get one for free!" and handed her a trinket.

Then he looked at me up-and-down and added, "Yeah, you'd have to pay".

Portrait Of Man In Santa Claus Costume.

40. All in the Family

Standing in the rain at night, after two years of dating, I think she is about to tell me that she loves me. Nope. She tells me that she is in love with my brother and has been dating me to get closer to him. I told my brother and he said, "Heck no! Screw her!"

Young couple, outdoors, standing face to face.

41. Out to Lunch

Years ago, when sitting at work, a buddy of mine, a guy I hadn't seen in years, came out of nowhere to say hi. I was thrilled to see him. He was only stopping by quickly though, but could hang out with me in a couple of weeks. I wrote his name and number on a post-it note and stuck it in my wallet. Keep in mind, we share the same first name, and I wrote down his first name on said post-it.

Ok, while keeping that in mind, two days later my roommate and I go to the local bar/pizza place we always go to for lunch. We have a nice waitress and everything is going well. When we're done eating, I put down my debit card to pay. The waitress comes back and is furious. Like, insanely ticked off.

She tells me she doesn't have to deal with this at work and that I'm a jerk like every other guy. Just rips into me while I have a blank look on my face. Tells me that she told the manager I'm not allowed to come back. Me and the roommate are pretty miffed. Welp, it turns out the post-it note with my buddy's number stuck to the back of my debit card, and she thought I was giving her my number. So this was a rejection where I wasn't even trying to pick up the girl. So that sucked. Still bugs me to this day.

Angry bartender.

Sources:  Reddit, , , ,

More from Factinate

Featured Article

My mom never told me how her best friend died. Years later, I was using her phone when I made an utterly chilling discovery.

Dark Family Secrets

Dark Family Secrets Exposed

Nothing stays hidden forever—and these dark family secrets are proof that when the truth comes out, it can range from devastating to utterly chilling.
April 8, 2020 Samantha Henman

Featured Article

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.

Madame de Pompadour Facts

Entrancing Facts About Madame de Pompadour, France's Most Powerful Mistress

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.
December 7, 2018 Kyle Climans

More from Factinate

Featured Article

I tried to get my ex-wife served with divorce papers. I knew that she was going to take it badly, but I had no idea about the insane lengths she would go to just to get revenge and mess with my life.

These People Got Genius Revenges

When someone really pushes our buttons, we'd like to think that we'd hold our head high and turn the other cheek, but revenge is so, so sweet.
April 22, 2020 Scott Mazza

Featured Article

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but few people know her even darker history.

Catherine of Aragon Facts

Tragic Facts About Catherine of Aragon, Henry VIII’s First Wife

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but very few people know her even darker history.
June 7, 2018 Christine Tran

Dear reader,

Want to tell us to write facts on a topic? We’re always looking for your input! Please reach out to us to let us know what you’re interested in reading. Your suggestions can be as general or specific as you like, from “Life” to “Compact Cars and Trucks” to “A Subspecies of Capybara Called Hydrochoerus Isthmius.” We’ll get our writers on it because we want to create articles on the topics you’re interested in. Please submit feedback to contribute@factinate.com. Thanks for your time!

Do you question the accuracy of a fact you just read? At Factinate, we’re dedicated to getting things right. Our credibility is the turbo-charged engine of our success. We want our readers to trust us. Our editors are instructed to fact check thoroughly, including finding at least three references for each fact. However, despite our best efforts, we sometimes miss the mark. When we do, we depend on our loyal, helpful readers to point out how we can do better. Please let us know if a fact we’ve published is inaccurate (or even if you just suspect it’s inaccurate) by reaching out to us at contribute@factinate.com. Thanks for your help!

Warmest regards,

The Factinate team

Want to learn something new every day?

Join thousands of others and start your morning with our Fact Of The Day newsletter.

Thank you!

Error, please try again.