Making the first move can feel terrifying. People love to say the worst that can happen is getting a simple “no,” so you might as well shoot your shot. But as it turns out, “no” isn’t always the harshest response on the menu.
One Redditor asked men to share the most brutal things women have said to them, and some of these rejections make a polite decline sound downright sweet. We’ve rounded up their wince-worthy stories below—brace yourself.
#1

This wasn’t on her, but I still think about how awkward it was and how I wanted to [disappear].
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.
I would find out later this all was a prank devised by my friends, and still can’t believe I bought it. I can’t remember the exact detail on how my friends “discovered” the identify of the girl, but they gave me the info one day and I took it as real.
I knew of this girl at school, but had never talked to her before. I was walking to class with my buddies, we see this girl in the hallway take a turn and is heading away from us to class. My buddies get on me to “go ask her out man!!! She wants to hang out with you”. They get me pumped up enough to go chase her down in the hallway. I get to her and say “Hey (her name here), I got your notes and definitely would be interested in hanging out sometime with you”. The look of puzzle and confusion on her was so incredible, It immediately hit me that this was all a joke put on by my buddies. She says back to me “I have no idea what notes you are talking about, and I have no idea who you are. And if you can not talk to me again, that would be great.” I still get hit with that random memory and it hits me in the chest just like it did then.
NearbyCow6885:
With friends like that, who needs enemies.
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.
I would find out later this all was a prank devised by my friends, and still can’t believe I bought it. I can’t remember the exact detail on how my friends “discovered” the identify of the girl, but they gave me the info one day and I took it as real.
I knew of this girl at school, but had never talked to her before. I was walking to class with my buddies, we see this girl in the hallway take a turn and is heading away from us to class. My buddies get on me to “go ask her out man!!! She wants to hang out with you”. They get me pumped up enough to go chase her down in the hallway. I get to her and say “Hey (her name here), I got your notes and definitely would be interested in hanging out sometime with you”. The look of puzzle and confusion on her was so incredible, It immediately hit me that this was all a joke put on by my buddies. She says back to me “I have no idea what notes you are talking about, and I have no idea who you are. And if you can not talk to me again, that would be great.” I still get hit with that random memory and it hits me in the chest just like it did then.
NearbyCow6885:
With friends like that, who needs enemies.
Report
25points
#2

She berated me for 2 minutes calling me fat, loser, ugly with all of the above in combinations. I was 13.
I had kids who bullied me and said “that was rough man, I’m sorry”.
NobodyLost972:
Imagine being such a jerk even your bullies we're like "damn bro, that's rough"
I had kids who bullied me and said “that was rough man, I’m sorry”.
NobodyLost972:
Imagine being such a jerk even your bullies we're like "damn bro, that's rough"
Report
19points
#3

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.
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.
18points
#4

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.
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.
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17points
#5

Girl here. He laughed, called his buddies over (some of them were girls too) and proceeded to make fun of me. I’ll never forget that feeling in my chest ever.
rivlet:
This happened to me in fifth grade. They chased me all over the playground shouting, "Why would anyone like you?! You're gross/a nerd/have glasses/stupid!". It went on for over ten minutes because they were just riling each other up to have a go at me.
I ended up standing my ground at some point and scratching one of them on the nose. I got sent to the principal's office and forced to apologize to them. Meanwhile, when I got home, my uncle spanked me so hard I couldn't sit down for a bit because I "attacked some boys".
My aunt had me write an apology letter to one of the boys because his mom was a patient of hers.
0/10, would not recommend.
rivlet:
This happened to me in fifth grade. They chased me all over the playground shouting, "Why would anyone like you?! You're gross/a nerd/have glasses/stupid!". It went on for over ten minutes because they were just riling each other up to have a go at me.
I ended up standing my ground at some point and scratching one of them on the nose. I got sent to the principal's office and forced to apologize to them. Meanwhile, when I got home, my uncle spanked me so hard I couldn't sit down for a bit because I "attacked some boys".
My aunt had me write an apology letter to one of the boys because his mom was a patient of hers.
0/10, would not recommend.
Report
15points
#6

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.
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.
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14points
#7

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.
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.
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14points
#8

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.
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.
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13points
#9

Furiously: "Don't ever smile at me again like that. You're ugly and I do *not* fancy you."
The kicker was, I saw her outside of school, at a shop, with one of her parents. And all I did was smile at her because hey, there's someone I know from school. I was under no illusions that she had any interest in me. Still emotionally devastated to the point where it makes me wince to remember, 36 years later.
Nebraskabychoice:
You can't see it, but I am smiling at you RIGHT NOW.
The kicker was, I saw her outside of school, at a shop, with one of her parents. And all I did was smile at her because hey, there's someone I know from school. I was under no illusions that she had any interest in me. Still emotionally devastated to the point where it makes me wince to remember, 36 years later.
Nebraskabychoice:
You can't see it, but I am smiling at you RIGHT NOW.
Report
13points
#10

She said “(my last name) you make me sick”. That was over 50 years ago and I remember it like it was yesterday.
ModernDayTiefling:
"Lovesick?" 👉👉
ModernDayTiefling:
"Lovesick?" 👉👉
12points
#11

I had this girl friend who was crazy into one of the other guys in our friend group but was really shy. One day she was feeling confident and started flirting with him.
He said "You know, you're so weirdly attractive. Like not in a conventional way, but I bet there's someone who's super into it."
Here's the twist: he actually had a crush on her. He thought he was flirting back.
kopitar-11:
He was thinking like a teenage boy.
He said "You know, you're so weirdly attractive. Like not in a conventional way, but I bet there's someone who's super into it."
Here's the twist: he actually had a crush on her. He thought he was flirting back.
kopitar-11:
He was thinking like a teenage boy.
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12points
#12

I'm a woman and was only the witnessing bartender, but I still caught second hand damage:
I was working a Friday night shift covering at another bar in the chain I worked for, and saw a guy spend about twenty minutes working up the courage to go up to a stereotypically preppy pretty girl and her friends. He looked like a nice enough lad, shy, a little nerdy, but looked well put together and decently handsome (I guess? Idk, I'm into women).
He started with some opening greeting line I didn't hear, she interrupted him with an abrupt zip motion across the air and a curt "What car do you drive?"
He stuttered out a suddenly off-balanced "Uh.. Ford Fiesta?" and she'd rolled her eyes and fully turned her back on him before he'd finished pronouncing the 's'.
I felt bad for the guy and couldn't help but be a little terse to her thereafter. If you're not interested, that's more than fair enough, but there was no need for that level of callousness.
NihatAmipoglu:
He dodged a bullet tbh.
I was working a Friday night shift covering at another bar in the chain I worked for, and saw a guy spend about twenty minutes working up the courage to go up to a stereotypically preppy pretty girl and her friends. He looked like a nice enough lad, shy, a little nerdy, but looked well put together and decently handsome (I guess? Idk, I'm into women).
He started with some opening greeting line I didn't hear, she interrupted him with an abrupt zip motion across the air and a curt "What car do you drive?"
He stuttered out a suddenly off-balanced "Uh.. Ford Fiesta?" and she'd rolled her eyes and fully turned her back on him before he'd finished pronouncing the 's'.
I felt bad for the guy and couldn't help but be a little terse to her thereafter. If you're not interested, that's more than fair enough, but there was no need for that level of callousness.
NihatAmipoglu:
He dodged a bullet tbh.
Report
12points
#13

Female here he said "I've been thinking about whether I want or need you in my life and the answer to both is no".
AppropriateAmoeba406:
“I don’t like or respect you. We shouldn’t be together.”
We stayed together for another YEAR! Because we were both idiots, apparently.
AppropriateAmoeba406:
“I don’t like or respect you. We shouldn’t be together.”
We stayed together for another YEAR! Because we were both idiots, apparently.
Report
10points
#14

She said ‘Aww’ and patted my shoulder. I’ve never recovered.
EasyMode556:
This isn’t too far from when I mustered all the courage I had to call a girl I thought was cute and ask her to prom. Her response was to go “awwwww, that’s so cute!” like I was some small child. She said no of course.
She wasn’t trying to be mean but it was a devastating blow. Like at least take me seriously and treat me as a peer, instead of some confused puppy?
EasyMode556:
This isn’t too far from when I mustered all the courage I had to call a girl I thought was cute and ask her to prom. Her response was to go “awwwww, that’s so cute!” like I was some small child. She said no of course.
She wasn’t trying to be mean but it was a devastating blow. Like at least take me seriously and treat me as a peer, instead of some confused puppy?
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10points
#15

"Hmm, I'm not sure I even like you as a friend, but sure you can take me out why not."
My confidence was torched for years and that was the worst most awkward date of my life lol.
MaxMouseOCX:
... You still went on the date... Shouldn't have done that.
OP:
My brain went into "so you're saying there's a chance" full denial mode lol
Besides backing out is almost worse it was all bad.
10 years later and I wake up in a cold sweat sometimes remembering lmao
My confidence was torched for years and that was the worst most awkward date of my life lol.
MaxMouseOCX:
... You still went on the date... Shouldn't have done that.
OP:
My brain went into "so you're saying there's a chance" full denial mode lol
Besides backing out is almost worse it was all bad.
10 years later and I wake up in a cold sweat sometimes remembering lmao
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10points
#16

Pretty blonde girl used to always tease me in high school and let me play with her hair and stuff all the time. One day, I finally built up the courage to ask for her phone number in front of other classmates. She loudly says "(my name), NOOOOO! 🤣" and laugh out loud. A few other guys and girls laughed at me with her. Still haven't recovered from that one.
deathmetalreptar:
Let you play with her hair?
Jesta23:
She might’ve liked you but you weren’t “cool” enough to admit to her friends.
deathmetalreptar:
Let you play with her hair?
Jesta23:
She might’ve liked you but you weren’t “cool” enough to admit to her friends.
Report
10points
#17

So I’m a girl, but when I was in 6th grade I had a crush on an admittedly nerdy guy in a few classes of mine. I loved how smart he was and wasn’t a flirt. One day my mom comes to school and says we’re leaving and never coming back (fleeing DV) and I decided to just spill my guts. “Phillip, I have had a big crush on you.” He looks at me and says “Ew.” I was absolutely mortified.
piccolo_bsc:
Wasn't it more like a "he's a kid and still thinks girls are ew" ew rather than him finding you ew?
piccolo_bsc:
Wasn't it more like a "he's a kid and still thinks girls are ew" ew rather than him finding you ew?
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10points
#18

I unintentionally destroyed a boy once who asked me out in high school. He and I never really talked, but he sat in front of me in chemistry class. One day, he was stretching at his desk with his back arched over the back of his chair and he looks at me (with his face upside down) and says with a goofy grin, “Will you go out with meh?”
I responded, “Are you joking…?” Because I genuinely couldn’t tell given how he delivered it. Turns out he was not. He turned back around and never spoke to me again. Looking back, I probably came off as horrible and mean—like I was saying the thought of dating him was laughable, a joke. I think about it every now and again and feel terrible. I really wasn’t trying to embarrass him!
MsAnthropied:
I did that. I was picked on and bullied at the school in my hometown. One of the favorite ways to do so was for the popular guys to dare one another to ask out an ugly girl and they often picked me. I wasn't actually ugly though. I was just unkept and poorly dressed due to poverty and neglect. When I moved in with Dad, I suddenly had clothes that were bought to fit me instead of hand me downs and it was possible to be clean and hygienic. The first few times someone asked me out, I responded with hostility because I thought it was the same old stuff starting up at a new school. It wasn't until years later at a reunion of sorts that one of them asked me why I was nice to him until he asked me out that I realized he had meant it back then. I awkwardly apologized and explained things to him and he was fine, but I still felt terrible for lashing out at the others.
I responded, “Are you joking…?” Because I genuinely couldn’t tell given how he delivered it. Turns out he was not. He turned back around and never spoke to me again. Looking back, I probably came off as horrible and mean—like I was saying the thought of dating him was laughable, a joke. I think about it every now and again and feel terrible. I really wasn’t trying to embarrass him!
MsAnthropied:
I did that. I was picked on and bullied at the school in my hometown. One of the favorite ways to do so was for the popular guys to dare one another to ask out an ugly girl and they often picked me. I wasn't actually ugly though. I was just unkept and poorly dressed due to poverty and neglect. When I moved in with Dad, I suddenly had clothes that were bought to fit me instead of hand me downs and it was possible to be clean and hygienic. The first few times someone asked me out, I responded with hostility because I thought it was the same old stuff starting up at a new school. It wasn't until years later at a reunion of sorts that one of them asked me why I was nice to him until he asked me out that I realized he had meant it back then. I awkwardly apologized and explained things to him and he was fine, but I still felt terrible for lashing out at the others.
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9points
#19
I was talking to a girl on nye. It's 11:50 pm. They're doing the count for the ball drop. I'm standing against a wall, drink in one hand, the other hand around her waist. She has her arms around my shoulders. I off-handedly mentioned I was broken up with recently by a woman. Her jaw dropped, removed her hands from my shoulders, said "omg I thought you were gay I'm so sorry", and then disappeared into the crowd.
It's been two months, I think I have thought about it every day since.
It's been two months, I think I have thought about it every day since.
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9points
#20

Long story, but really funny in retrospect.
Liked a girl at church, this was around the age of 11/12. I remembered a story my dad told me where he would send cute little notes to my mom through feiends to let her know he liked her.
So I started to do that with this girl, passed her notes every so often.
Unbeknownst to me, I had competition from one of the other guys in Sunday School. So he caught wind of my cute idea, forged a note in my handwriting, and completely sabotaged me.
Whatever he wrote, it was enough to make this girl's father approach my parents, show them the note, and then they all had to sit down and have a chat with me about not being "pursuant" in such an aggressive and creepy manner.
The girl's older sister also approached me a week or so later and told me to leave her sister alone, and that I wasn't allowed to talk with any of them anymore.
Then, the girl apologized and told me she had hated my guts anyway.
Thanks, Jared, wherever the hell you are, sure was a good prank!
HotWaffles5:
That wasn’t Christianly of him. Jared is a jerk.
Liked a girl at church, this was around the age of 11/12. I remembered a story my dad told me where he would send cute little notes to my mom through feiends to let her know he liked her.
So I started to do that with this girl, passed her notes every so often.
Unbeknownst to me, I had competition from one of the other guys in Sunday School. So he caught wind of my cute idea, forged a note in my handwriting, and completely sabotaged me.
Whatever he wrote, it was enough to make this girl's father approach my parents, show them the note, and then they all had to sit down and have a chat with me about not being "pursuant" in such an aggressive and creepy manner.
The girl's older sister also approached me a week or so later and told me to leave her sister alone, and that I wasn't allowed to talk with any of them anymore.
Then, the girl apologized and told me she had hated my guts anyway.
Thanks, Jared, wherever the hell you are, sure was a good prank!
HotWaffles5:
That wasn’t Christianly of him. Jared is a jerk.
Report
9points


