Weirdos, losers, creeps and wimps, it takes all kinds...to really make these pick-up stories bizarre. Check out of of the worst flirting you've ever heard of!
A Girl Doesn’t Care About Her Boyfriend…or His Girlfriend
“Gave a speech for a class once, and after my speech ended I went to get a drink. On the way back to class, a cute girl from the class was in the hall, looking like she was waiting for someone. I assumed her boyfriend, since he was also in the class with us. She saw me and lit up, asked if I wanted to join her for a cig (I don’t smoke but I obliged to keep her company since other people speeches stink) and we headed outside.
We joked around a bit, she tried flirting but I have a gf and I didn’t reciprocate. Figured she was just a bubbly person. Right when we’re about to head back, she hands me a slip of paper with her number and says ‘you should give me a call later today and we can get to know each other better.’ I ask her about her boyfriend and she says ‘he’s working later.’
I of course politely declined, went back to class and spent the rest of the day wondering why the porn script scenarios always happen when I am in a happy, committed relationship but never when I am single. When we got back to class, she gave her bf a peck on the cheek and sat back down next to him.”
A Paranoid Weirdo Has a Lot Of Odd Questions
“I was walking down the street, in the middle of December, hands stuffed in my peacoat, walking behind a young man who looks pretty paranoid. He finally stops and asks,
‘Do… Do you have a gun?’
I pull my hands out of my pocket and shrug. No, no gun.
‘Oh. Do you have any drugs?’
‘Nope dude, sorry.’
‘Oh. Do you have a boyfriend?’
Priorities man, priorities.”
A Creeper At A Pool Gets Really Weird With a Pregnant Woman
“Let me start my story be stating the fact that I am very, very pregnant. I am so hugely and obviously pregnant that people feel the need to approach me in public and offer their condolences for how pregnant I am. I am not kidding. Men and women alike have stopped me just to say ‘You poor thing.. I am so sorry. You look miserable.’ That is how pregnant I happen to be at the moment.
That being said, my favorite place to be in the entire world is in a pool. Swimming makes me feel like a normal human being.. The swelling in my hands and feet goes down, the pressure on my hips vanishes, my belly button goes back to being an innie.. It’s wonderful. Anyway, last weekend my friend texts me and asks if I’m up for a swim. I certainly am up for a swim; however, it’s a little after 8:30, and my condo’s pool closes at 9. We decide to go to the pool at her apartment complex, as it is open until 10.
We make our way out to the pool, where the only occupant is a middle-aged guy wearing a swimcap and goggles. I don’t pay him any mind, just figured it was a resident doing some evening laps. No big deal. He watches us get in the pool, and says something I can’t make out.. I ask him to repeat himself, and he says ‘I’ll just swim over here.’ Um, okay. So my friend and I start chatting about nothing in particular, and Mr. Swimcap starts awkwardly butting into our conversation. He wasn’t trying to add to it, he would just ask random questions, only we couldn’t make out what he was trying to say. So we kind of brush him off, and he starts swimming around the pool, and keeps ‘accidentally’ swimming into us. (Keep in mind he’s wearing goggles.) So we move to another part of the pool and try to act like nothing’s happening. He stops trying to swim into us and starts just staring at us. Then he says something. The conversation goes as follows:
Me: ‘Dude, I can’t understand what you’re trying to say.’
Him: ‘WOULD YOU WANNA GO ON A DATE?’
Me: awkward pause ‘…Are you talking to me, or her?’ motions toward my non-pregnant friend
Him: ‘YOU. I THINK YOU’RE REALLY ATTRACTIVE. DO YOU WANNA DATE?’
Me: ‘Um.. I’m very flattered, but no thank you.’
Him: ‘SO YOU DON’T WANNA DATE?’
Me: ‘Yeah. I don’t want to go on a date with you.’
Him: ‘YOU HAVE A MAN?’
Me: ‘Yes. I have a man. And we’re fixing to have a baby.’
Him: ‘DO YOU LIVE TOGETHER?’
Me.: ‘Yes we do.’
Him: ‘SO YOU DON’T WANNA GO ON A DATE.’
Me: ‘Dude. No. I don’t want to go on a date with you.’
Him: ‘..BUT WOULD YOU?’
Me: ‘Would I what?’
Him: ‘GO ON A DATE WITH ME. I THINK YOU’RE A REALLY ATTRACTIVE PERSON.’
Me: ‘No! I’m done talking to you now. Please leave us alone.’
I go back to my friend and we start discussing exit strategies, as the guy continues to talk to himself. Luckily my friend’s male neighbor decided to come hang out for a bit. Mr. Swimcap starts ranting at the neighbor about who knows what (mortgage companies, maybe?) so we try to enjoy the remainder of our time in the pool. A little while later the security guard comes by to lock up, my friend, her neighbor, and I bolt out of there while Mr. Swimcap is gathering his things. Good Guy Neighbor later walks me to my car to ensure there are no creepers lurking about.”
Defended From A Random, By A Random!
“I was walking down a street in Berkeley often lined with older homeless guys and panhandlers. It was a warm day so I was wearing a cute, but modest, black and white polka dot 50s style dress that always got me a lot of attention from the men. Anyways, walking by two older guys sitting on the sidewalk near each other, but far away enough to not encroach on each other’s change-seeking turfs when the first one I pass hollers something to the effect of ‘Hey Girl, let me see that dress on my bedroom floor!’ To which the second homeless guy responds, without missing a beat, ‘Hey don’t you talk to my wife that way, she’s a lady!'”
How Do You Tell Your Grandkids That You Met In A Police Car?
“I was arrested in high school for a spontaneous bout of stupidity and as I got into the cop car I realized that there was a teenager doing a ride along with the cop. I didn’t think much of it seeing as that I was, you know, pretty busy focusing on how much trouble I was going to be in.
A few days later, as I settled into my permanent-grounding, I got on Facebook. Lo and behold, I have a Facebook message. The boy doing the ride-along with the cop had written down my contact information and found me on Facebook just so that he could send me
‘Hey Girl, I just wanted you to know that I hated arresting a woman as beautiful as you.'”
Father A Year, This Guy
“I was hanging out with a friend the day before Easter. She had to drop by another friends house for a quick errand so I went with her. They had an Easter party going on for this woman’s children and a few of their friends. The parents were having a BBQ and the kids had done an Easter egg hunt and moved on to painting pictures for their parents. A normal enough fellow started chatting with me and after about ten minutes with the group I realized he was there with his two year old and the baby’s mum. I wasn’t sure if they were together but I just assumed they were and left it at that. So when we went to leave, I was totally taken aback when he pulled me from the doorway where everyone was saying goodbye to each other. He shook my hand and whispered ‘shhhhh… It was so great to meet you. Shhhhh.’ He put his finger to his lips, winked, then turned me back around to face the group. I just stumbled through my normal goodbyes and left without acknowledging him. While walking away, I unfolded what he’d slipped me while shaking my hand.
It was his number and a note that said ‘UR cuute. Txt me’… Torn from a large chunk of the Easter painting his child had proudly handed him ten minutes before.”
Two Comedians Drive A Couple Away
“This was at a college bar in California. Anyways, this young couple were sitting together at the table next to mine and it was apparent they were dating (holding hands, smiling at each other constantly etc…) and were minding their own business when out of nowhere a guy in his early twenties and clearly a bit drunk walks up to their table and looks at the girl for a second then glances at the guy and says: ‘Hey guy! Mind if I talk to your sister?!’ Well, hearing this I look over at the boyfriend and he has this look on his face that just screams, what the heck? So here’s how the rest of the conversation goes…
Boyfriend: She’s my girlfriend man, so yeah I mind.
Guy: You’re dating your sister? Isn’t that illegal?
B: No, she’s not my sister(clearly agitated), she’s my girlfriend.
G: Ohhhhh. So she was your sister… and now she’s your girlfriend?
B: No, leave us alone kid(at this point the drunk guy turns around and yells for his friend to come over)
G: Hey (Guy 2)!!! Come over here! This guy is dating his sister!!!
So next thing I know this well groomed/ dressed guy (clearly gay) comes over to the table to see what kind of trouble his buddy is getting into.
Guy: He’s dating his sister (Guy 2)!
Guy 2: Isn’t that illegal?
Guy: That’s what I said!!
Well now the couple are pretty angry and the girl suggests to her boyfriend that they go somewhere else. As they gather their things and start to walk away the second guy walks up to the girl and says:’Hey, would you mind if I talk to your brother?’ And this look of horror spreads across her face as she realizes this gay guy wants to talk to her man. The couple basically ran out of the bar and the two guys busted up laughing from the reaction they got.”
Sometimes Being Sketchy Works, Apparently
“Walking down the main street of a medium sized town with my girlfriend and her sister. Alright looking guy in alright looking car, maybe about 22-25, pulls up, and shouts to the sister, ‘Hey, you, in the blue. Come get in the car, go with me.’
She shrugs, walks over, talks to him for a few seconds, gets in the car.
They were married four months later. Last I heard, it was still going strong, but that’s been awhile.”
He’ll Come Runnin’
“I was at a beach with three other friends. It was a weekday, so there wasn’t a crowd, but a bearable amount of people to handle.
We were enjoying ourselves and my friend and I were just floating about and talking, when I then notice this tan guy not too far away from us. He was staring straight at us. With an extremely creepy and perverted grin.
We decided to swim back to shore and started to take pictures, and guess who decides to come along? Creepy tanned guy. At this point we still really haven’t reacted, but then he starts RUNNING back and forth on the beach, never taking his eyes away from me and my group.
He eventually starts doing his little running routine closer and closer to us. When we thought it couldn’t get weirder than that, it did. Every time he ran towards us, he slowed down, eyed us up and down then smiled his creepy smile and began CHANTING. He was chanting actual gibberish – no English words, or any language you’d recognize. It was like he was performing a ritual on us. It was creepy as hell.”
A Weirdo Loves Her Long Hair
“I have very, very long hair. It reaches below my knees. If it helps visualize, I’m a slim female.
‘DAYUM, GIRL! Your hair be crazy! Like a horse tail! Hey, you should know I’m a total stallion, babe.’
This guy leans in really close and starts stroking it. I got out of there as fast as possible. He calls after me in a gruff plead, ‘Aw, c’mon, girl, lemme see if all yo hair be long ‘n beautiful!’
I’ve also had a dude just grab a breast out of nowhere. I punched him on the ear.”
When Flirting Goes Very Very Wrong
“I don’t often go out, let alone to bars. I’m not a drinker but I decided to humor my boredom and go out by myself. I put on a nice flora spring filled dress and hit the town. I’m at the bar sipping away at whatever I had bought that night when I spot a cute guy sitting at a table drinking with two other guys. He’s laughing, having fun and his smile is attractive. Now I am not the type to approach at all, shoot, I haven’t even had a boyfriend out of school that one time. I’m pretty quiet and shy, tend to avoid these kinds of situations all together, but this night I had seemed to have bolstered all my courage that I had stored over the last 21 years for one. single. move.
I was going to buy that nice smiling dude a drink.
I knew a large percentage of guys liked this maneuver thanks to the internet. I would simply ask the bartender if she knew what the guy was drinking and if so, if she could make another for him, deliver it and I’ll cover it. I thought it was perfect. It wasn’t pushy, in his face flirting. If he wasn’t interested, no big deal, he didn’t have to approach me/engage in conversation or heck, even thank me. I didn’t think anything could go wrong.
Bartender escorts the drink over to the table, guy seems curious, butterflies start vomiting in my stomach. He enquirers and she mentions to me, I offer a friendly smile and a wave. They all laugh. Him, his mates, laugh at me. And not a nice laugh, not a ‘oh hey you just got picked up by a chick, haha, that’s it bro you got swagger’ no it was ‘Holy smokes you got picked up by a fat chick, you must be a pig magnet sucks to be you’ laugh. One of his mates slap him on the shoulder and that’s when he does it.
He raises the drink I bought him in a toast, then dumps it out behind him into the potted plant.
And here is the part of the story where I wish I could say I stormed over there and slapped him. I wish I could say I tipped my own drink on him. Oh No I wish I could say Batman swooped out of a dark corner of the bar and punched him in the nuts.
However, I cannot. I simply turned around immediately and left, feeling the most ashamed, humiliated, embarrassed, fat, ugly, worthless, downtrodden I ever had. At least I made it out the door before the crying started.
I haven’t been to a bar since.”
A Woman Lays It On Think and Creepy
“I get a new job teaching computer courses to adult classes of adult learners. I go to check out an apartment I found on Craigslist near my new job.
The renter and I exchange some emails. I tell her about my job, she tells me about the nutrition supplements she sells. She also tells me entirely too much about her life, her ex-husband, and her custody battle over her 13-year-old son. Boundary issues. But I respond very sympathetically towards her, because I’m a people pleaser with my own boundary issues. We hit it off!
The address is a house, and I figure it must be a duplex of some sort. The renter invites me in; she’s a 40 something woman, fairly attractive, and I’m in my early 20’s at the time.
She introduces me to her son who’s in the living room playing Guitar Hero. Then she shows me the room which is just off the living room, separated by a curtain.
I tell her Im surprised–I thought she’d listed an apartment. No, she explains, it’s just the room; but it comes furnished with the dresser and this waterbed.
Don’t worry about the curtain, she says. You’ll have plenty of privacy–you just need to turn this fan on. She turns the fan on.
She sits on the bed, and asks me if I like waterbeds. I tell her I’ve never been on one. She invites me on the bed with her. I demure. She cajoles. She promises me it’ll be fun.
I don’t get hit on much. I’m a good looking guy, but quiet, and I’m just not used to having signals sent my way. But at this point I put it together that she is inviting me to engage in sexual shenanigans.
While her son is 15 feet away.
On the other side of a curtain.
I was aroused despite my common sense. But common sense won the day.
I get out of there as politely as possible, tell her I have to think the room situation over.”
Nothing Weirder Than a Foot Fetish In Public
“I was waiting for the last train from Paris to go back to my good old suburbs, so this is right after midnight, the station is quite empty, only a few people left around. Should probably mention I’m a girl, and alone.
Anyway I have about 15 minutes left to wait, and this old guy just comes and sits next to me. After a few minutes he gets the courage to ask me:
Could I ask you a favor?
Oh, no nevermind, it’s ok..
He looked really sad and miserable about something, so I try and be nice and I insist, thinking he’s just going to want to talk about something:
Could I.. see you feet?
I think you have beautiful feet… could I just see them? I won’t touch or anything, I just want to look! You can keep your socks on if you want.
At that point I’m quite weirded out, I was wearing some converse, and this guy is making me feel bad for telling him I don’t want to show him my feet >_<
He kept insisting with this miserable look on his face, he even suggested to get on the next train and if there’s too many people I don’t have to if I’m being shy or something..
I actually felt like I had to apologize to him because I didn’t want to show him my feet.”
A Man Stupidly Brags About His Conquests
“When I was going to college I was sitting in the cafeteria with a group of like 11 people who all knew each other and were D&D nerds together. There were about 4 very attractive girls in this group.
One kind of sweat-smelling, mouthbreathing new-ish guy who had only recently ‘joined’ our little group leans over to one of the girls in the group brags about how he can do a perfect Zapp Brannigan impersonation. She asks to see, and he goes ‘If I said you had a beautiful body, would you take your pants off and dance around a little?’ in Zapp’s voice. We laugh in that awkward ‘not sure if rapist’ way. I have to leave for class.
The next day he gets to the table before the girl from earlier does, strikes a heroic pose, and says ‘Kipf, I have made it with a woman. Inform the men.’ The girl is mortified that he not only told everyone, but told everyone in Zapp Brannigan’s voice. Fortunately he had the good sense to be too embarrassed to show his face again after that.”