People From Around The World Share Their Cringey Flirting Stories

People From Around The World Share Their Cringey Flirting Stories

Flirting is a fine art. When you first start out, it takes time and failure to master it. Some people never manage to be more than minimally uncomfortable; others never learn how to be less than disastrous.

But if you're looking on pointers on what not to do when flirting, these folks below have you covered. They recently went online to share their cringiest flirting stories. Some were the victims, others the perpetrators. But all will make you grateful that you were in no way involved.

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60. Big daddy

I work at Starbucks and I was making drinks and calling names when I had to call one out to a "Big Daddy" he responded by saying "awww yeah right here baby."

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59. Love sick

When I was seven I had a crush on this girl in my class. I was the only boy in the class who actually liked girls by this age and I tried to hide it. At the same time, though, I really wanted her to be my girlfriend, whatever seven-year-old me thought that entailed.

So I tried a bunch of different things. I invited her to my birthday party, where my brother made fun of me the whole night, I always picked her when we played 7up, stuff like that. My favorite was when it was Valentine's Day and I wanted to impress her, so I tried to smell really good, I didn't own cologne because I was seven, so I covered myself in baby powder. No joke like head to toe underneath my clothes was covered in baby powder.

On top of that, I made this huge Valentine's Day card that had this picture of me and her holding hands I drew myself. When it came to hand out the Valentine's, we did, but I was so nervous when I did it, and everyone started mocking me saying I had a crush on this girl. It all became a little too much for me and I vomited onto my crush.

If that weren't enough, upon realizing my mistake, I blurted out, "I'm so sorry, I love you!" I did this as I was trying to clean the vomit off of her with my bare hands. Safe to say she didn't feel the same way.

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58. Lose now, win later

I was talking to a girl and her friend in a nightclub and it was going well so I figured I'd whip out the old iPhone 3G (long time ago I know) to ask for her number.

I was far too enthusiastic and it went flying out my hand and landed on the floor and reset so it displayed the Apple logo.

I just picked it up and said sighed "never mind" and walked away with my shame.

Little did I know the girl who is now the mother of my child watched it happen and was laughing from afar.

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57. Cringey because you didn't flirt

I had a very pretty friend of mine from college stop in town and call me to catch up after work. We go to happy hour and she starts talking about how she has only slept with one guy and she wants that to change. She then goes on about how her friend I had slept with had a very high opinion of me.

We put back a few drinks and then I left because I had to get up for work the next day. I told her she was really pretty and shouldn't have any trouble hooking up with a guy of her choosing.

A year later it dawns on me...

I swear I'm usually not a social idiot.

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56. The ladies love deductive reasoning

So back when I started learning how to flirt a few prior successes made me decide to try my luck with this intimidatingly hot girl. So I walk up her brimming with confidence tap her on her shoulder, she turns around and I said "hey" with a raised eyebrow. She's looking unimpressed so I follow up with: "Why would a girl like you feel the need to hide that pretty brown hair?" (Her hair was black at the time.)

She's smiling now; I've got this. She gets really close to me all giggly and bright-eyed asking how I knew her hair was brown. Her hotness shatters my false confidence and I start mumbling about her having freckles, genetic impossibilities and deductive reasoning... it was all downhill from there.

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55. Free shower

I was at a festival and went over to talk to a girl I was interested in. For some reason I tried to get her attention with a water bottle, that was unknowingly open. I absolutely soaked her with it. There is no coming back from that.

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54. Foul weather friends

I'm female. I wanted to try to flirt with the cute cop guarding my work building, so on my way back from walking in the rain without an umbrella, I tried to make small talk about the weather. What came out instead was:

"In case you didn't know it's raining outside just take a look at me, I'm nice and wet."

His face turned bright red and once I realized what just came out of my mouth I stuttered something like, "No, no, I mean....uhhh..."

And then I ran up to my office and hid the rest of the day. I never saw him again.

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53. Who's my cute little dinosaur?

I had a crush on this woman for ages. I was around 23 and she was 22 at the time. She was heavily into raving/clubbing at the time -- hardhouse specifically. Now, this girl Steph was really pretty but had a very unique bone structure to her face, the type models have.

So I was pretty smashed at a. show and we crossed paths in the club. Small talk ensued and I basically said: " Steph you are really hot and unique looking you have the bone structure of a velociraptor."

She was horrified and genuinely we spoke very little after this.

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52. Fetus and the beast

In high school, I was really into this one girl who would put herself down just to get others to compliment here. For example, she would say "I'm so dumb, I know I failed that test" and then wait for someone to say "Naah I'm sure you did well, you're very smart." As a dumb teenager I never really noticed it until after someone pointed it out that she was just fishing for compliments and now, as an adult, I freaking hate when people do it.

But anyway, her original prom date bailed on her days before prom and I saw it as an opportunity to step in and get this done. I was nervous, using my best jokes and one-liners from TV. It worked, I was getting somewhere but I could tell that her interest in me was waning a bit so I had to keep up the charm, keep talking, and... of course... I did so without thinking.

I asked her out to the prom, and she did her compliment-fishing things again, saying: "Why would you want to take me? I look like a fetus. You should take someone prettier."

To which I said: "What? are you crazy?!? I love fetuses, and the prettiest one at that!"

I didn't realize what I had said until after a 10-second awkward silence followed-by an "Um... I gotta go. I'll see you around."

I never actually did see her around, she just ignored me every time I would try to strike up a conversation or just shoot down any attempt real quick. I'm just so grateful she didn't bring it up to anybody to embarrass me because my god I could never live that down.

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51. Bad flirting with a happy ending

I had been invited to go with a friend to Chicago. We brought along a friend of hers, but someone I hadn't ever met. He was a cute guy though, and we talked a lot, had a lot of similar interests.

At one of the museums in Chicago, my friend wanted to go see a deep-sea movie, and I... can't do anything deep sea. Her friend offered to stay outside with me so we could both go look at the Lascaux cave painting exhibition, which was VERY exciting to me. It wasn't all just about the cave painting, but about ancient life, knapping, hunting, the way they made things, etc...

So I, not being able to control myself because I have 0 social knowledge and I'm also yeehaw country, at the exhibit about hunting specifically, ask this very cute guy I am very interested in if he knows how easy it is to skin a deer. He looks at me. I look up at him and keep. Going. My brain is screaming at me to stop but it has no control over my stupid honky mouth.

"Simple as getting a truck, a knife, a rope, and some rocks! You cut around the neck, make a kind of ruff, and tie the rocks into that. Then you tie the other end of the rope to the truck and drive slowly forward. It comes off like a sweater!"

This idiot dated me and married me instead of running for his life. Four years married this May. Love you forever, babe, through the brightest day and blackest night.

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50. Losing face

Was hitting on this girl in college, was a party we had going on in one of the halls (end of the term I think)

Things going well, both having drinks and stuff, just as I’m starting to “make a move in” for a kiss this guy walks past with his girlfriend on his shoulders and the girl I’m flirting with goes “I wanna do that!”

So, very hammered me picks her up, proceeds to walk her straight to the next hall, then I trip, she slips down and falls flat on her face, lots of blood pouring from her nose.

I stand up to see her on the floor like this, and stupidly say, “your face looks BRUTAL.”

She never spoke to me again.

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49. I look fabulous

I was at a gay bar a couple of months ago. There was this guy wearing the exact same shirt as me. I go up to him and say something like "Cool shirt!"

He responds: "Looks better on you."

My stupid response: "I know, but you still look ok in it."

Run away.

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48. My new pick-up line is "buh"

So a while back, I was at a used book store and this guy sidles up to look at the same section I'm looking at. I side-eye him, and holy crap he's cute. And he's wearing a Left 4 Dead shirt. I love Left 4 Dead! He's looking at a James Michener book. I love James Michener!

Maybe someone with more confidence and social skills would have started up a conversation, all "oh, do you read a lot of historical fiction?" or "oh, I notice you're looking at a James Michener book. He's one of my favorite authors."

But me, I'm basically Rainman-level awkward. He looks over at me, probably because he's noticed this dumpy thirtysomething staring at him dumbly, and smiles. Everything I had planned to say went out the window then. No questions, no flirty smile. Just: "Buh."

This is actually what I said. Freaking buh.

So he kind of gets this weird look on his face and says "excuse me?" and I can feel my face is bright red now and so I mumble, "I like your shirt. I like video games."

"Oh," he says, looking down at his shirt. "Thanks."

"Yeah, no problem!" I manage to squeak out. I barely finished my sentence before I fled the aisle. I am so smooth, you guys.

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47. I guess that's a compliment?

I was in my early twenties and found myself flirting with a handsome man who was flirting back in the cafeteria of a hospital where I was killing time before my OBGYN appointment.

I left as my appointment time was nearing and I knew there would be paperwork. Forward to the feet in stirrups and who walks in? It was the man from the cafeteria. He took a look at my lady parts and said, "Gee, you don't look like a mother of two." I was mortified.

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46. I don't care what anyone says: you're a legend

At my fourth or fifth college party, I noticed a girl who I'd seen a few times before and considered pretty cute. I went up to her and said, "Hey, I'm Josh, what's your name?"

She just looked me up and down for half a second and said, "Um, no," and turned her back on me and walked away.

I was so embarrassed that to detract attention from what just happened, I then grabbed a bottle from some random guy next to me and chugged for like ten seconds and threw the bottle at the wall yelling, "FOR NARNIA!"

Then while everyone was sort of quietly staring at me, I grabbed a ping pong ball from the BP game going on and shot it and made it and just said, "I'm out, nerds," and stumbled out the front door into the waiting arms of a cop.

Got breathalyzed, ended up in the back of the paddywagon... WITH THE GIRL WHO REJECTED ME. She was all like, "Hey so you're pretty good at beer pong, huh?" And I vomited in her lap. Not another word was spoken between us.

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45. You should never be allowed to talk to women again

My boyfriend was killed in a car wreck one year ago. He had to be cremated. I am in college, and at the time I was walking across campus when his mother texted me that the cremation had been done. I fell to the ground in tears.

A guy came up to me, picked me up off the ground and hugged me. I just cried into his shoulder and told him what had just happened, saying something like "my boyfriend died..." He said, "Well, do you want a new one?"

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44. That's some compliment

Upon finding out that I can't drink because of a medical issue, a guy told me:

"It must be hard for a guy to flirt with you considering he can't give you drinks and make you all stupid."


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43. Quite an offer

I had a guy at a bar notice I was Italian, and then proceed to tell me how great Mussolini was before asking me how I would feel about a "naked 40-year-old man lying on top of me for 30 seconds." I think it was supposed to be a pick-up line.

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42. Reading into it

My far-distant ex-boyfriend once stole my crutches... because he was mad I wasn't "getting out as much" (I had been hit by a truck) and he wanted to manipulate me into going to book club with him.

It was a feminist book club!

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41. You talk too much

I had a guy tell me "you were a lot more interesting before you started talking" and then continue to flirt with me. I don't know if that was an attempt at negging or what.

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40. Coffee with a twist

Just this morning I'm in line to order at Starbucks. The guy in front of me is casually flirting with the barista taking his order. He finally orders and she says, "This is the part where you give me $4.11." He said, "When is the part when you give me your phone number?" She said, "This is the part where I introduce you to my husband, he's standing right behind you." It was my wife.

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39. I think that's a 'no', dawg

Back in first year, I took a girl I'd had a huge crush on to see a movie. Near the closing credits, I leaned in to kiss her, and she leapt out of the seat and screamed "NO!!!!" at the top of her lungs in the middle of the theatre. Driving her home was pretty awkward.

After that I had a lot more confidence asking girls out, because I figured "What's the worst rejection that could happen? Scream in terror in front of more than a hundred people? Been there, done that."

Dating and flirting got a lot easier after that.



38. Everybody's got a price

He asked if I would sleep with him. When I said no, the proposal was spiced up with an offer of $35. I wasn't as much offended by the offer as I was offended by it only being $35.

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37. I picture this happening in a coffee shop

I once saw this guy wait for a girl's friend to go to the toilet, leaving her alone, then he danced this really goofy dance (he put his arms out to the side with his elbows bent, then basically bobbed his arms up and down) all the way across the room to her. Then - while still arm-bobbing - he said, "Hey... wanna dance?" To which she replied "no." He said "okay", then did the arm-bob dance all the way back across the room to where he had started in one slick motion.

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36. This is why people put 'fluent in sarcasm' on dating profiles

My failed flirting attempts usually involve girls not recognizing sarcasm. My favorite of these was, in response to her mentioning she was taking a class in race relations (or something like that), I replied, "That's interesting, I'm actually racist myself." Her eyes got real big and she got real quiet. "Are you serious?"

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35. Reagan is my wingman

For the first time in all my years on Reddit, I finally have the best possible response for an AskReddit thread.

During college I was invited to my friend's room to drink with her and her new roommate. After a few shots we started playing this game "F You" with some cards. The roommate kept going after me in the game, so it was obvious what was about to transpire.

My friend left her room (what a champ) and we immediately start getting hot and heavy. Just before things start getting interesting, she goes, "Stop stop stop!" I was worried and replied, "What?!"

I will remember this till the day I die. She replies, "You're a Republican, right? Because I can't hook up with any liberals."

I looked her straight in the eye and said, "I love Ronald Reagan."

Terrible flirting, but mission accomplished.

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34. Quite a feet

One time in college I was standing in the elevator in my dorm and this girl just stares at my feet and says, "You have really nice toes." I saw her in the elevator a couple weeks later and she says to me, "Hey, you're the guy with nice toes."

My toes are regular toes, they have a little bit of hair on them too. I have no idea what she liked about my feet, and I didn't care to find out.

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33. I just want to graft your face

One guy told me that my roommate's body "was bangin'" and that he wished he could morph my face on it. That was the last thing he ever said before I blocked him for good and he just couldn't understand why. Like, thanks for making me think that my face is my only redeeming quality, jerkwad.

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32. To be fair, that move killed in fourth grade

My buddy once sat nervously at a bar waiting to talk to a very attractive girl. He finally got up the courage to go talk to her but when he got close to her, he instead teasingly punched her in the back and ran away.

It remains the saddest male-female interaction I've ever seen.

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31. 'Original' doesn't mean 'good'

At closing time at a nightclub where I used to work, a guy says to these girls "Come back to my place, look what I can do."

He then walks about 10 feet away, drops his pants, bends over, and pees in his own mouth.

It didn't work, but man that sure was original.


30. Who are you wearing?

I had really been partying too hard and I should have gone home. Instead, I tried talking to this woman.

Me: Unlike the other guys, I know when to stop drinking. I know when I had enough.

Her: Yeah.

Me: So, what do you do?

Her: I work at Tupperware. I sell Tupperware.

Me: Oh, really, so are you wearing it now?

Her: What?

Me: Tupperware.

Her: ...

I still don't get how I could get so hammered that I mistook Tupperware for lingerie.

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29. At least she says what she wants...

Once, after a lonely and long night at the bar after which I went home alone, I made an OKCupid account. I made my profile picture one of me cuddling with a baby elephant, then passed right out on my bed.

I awoke to a raging hangover and a message in my inbox from a very scary woman who had written out a list of deranged things she wanted to do to me, including, but not limited to, "sticking that elephants nose up your butt like a muppet and blowing air out your mouth like a foghorn."

I deleted the account.

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28. Mrs. Robinson

When my girlfriend and her friend went to the corner store to get some smokes, her mom walked over and sat on the couch next to me, put her feet on my lap and basically told me to rub them. I just looked at her somewhat stunned and didn't say anything. She then pushed her heels into my crotch a bit and said, "Don't you like me?"

I got up and walked out the door to catch up with my girlfriend and her pal. Never told her about her mom, but after dating her for a few months, it became apparent she hits on everyone! That's just... so scuzzy.

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27. Death of a waitress

I was working as a cocktail waitress. A customer said, "do you want to have lunch with me in a cemetery somewhere?" Um...nope.

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26. Not like this

Some random guy in the bathroom of a library came up to me while I was washing my hands and said:"Hey man, how do I hit on girls? Actually, to be more specific, how do I hit on you? Not that you're a girl. I hope you're gay too. This is weird, we're in a bathroom. I've gotta go."

The guy in the stall and I had a good chuckle over that one.

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25. Shoulda quit after falling in the pool

Was a company party back around 1990, at the VP of Operations house. Entire company was there. Very young crowd, average around 25. One of the VP's assistants has way too many drinks, manages to fall in the pool fully dressed. Gets out of the pool, loses all his clothes, and is now walking around in just a towel.

Liz, a barmaid that we all knew, had been invited. She's playing pool in the pool room and this guy walks up as she's bending over to line up a shot, opens his towel, flashes her his junk and asks her, "Do you know what this is?"

Record-scratch/E.F. Hutton moment. I should mention that Liz wears glasses.

She squints over the top of her glasses, shrugs and says, "Well, it sort of looks like something I've seen before... only smaller."

We all chipped in for the tombstone.

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24. Popped your cherries

I worked at a frozen yogurt shop and some kid came up to the counter with the toppings as I was trying to clean it up and thrust his phone out at me. I just stared at it for a second and then asked him what he was doing. We just stared at each other for a good 15 seconds before he said "put your number in my phone". I was like, "no" and then he dropped his phone in the cherries so I had to clean that up too.

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23. Cheese and a kiss

I was in line at Subway.

I was friends with the girl who was making the sandwiches that day, and she was definitely cute. The guy in front of me was hitting on her as he made his sandwiches (he had like three or four, so he was giving her a hard time for a good 10 minutes while she prepared all of it).

When he finally paid, he grabbed and kissed her hand as she gave him his change, and said in the cheesiest voice I've ever heard, "Would you accompany me to the theater, milady?"

I could tell by her face that he was going way too far, so I tapped him on the shoulder and said, "Hey, that's my girl."

He goes, "BS, prove it."

I just about drew a blank when the girl reached over the counter and grabbed me and gave me a huge kiss. The dude turned totally red and ran out of the store.

Then she gave me extra cheese for free.

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22. The goo and you

Sigh... I was flirting with a girl in a bar (and it seemed to be going well). About a half hour into our conversation, I had one of those very strong sneezes (the ones that come out of nowhere and cannot be stopped). I ended up snotting into my hand and had a string of goo from my hands to my face when I pulled my hands away.

I just walked away.

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21. Your big mouth

Was joking around with a girl and made a lightly rude comment, which the girl rightfully took as a joke. She covered her ears and laughingly said "Oh, my virgin ears!" I thought I was being witty when I answered with "Is your mouth a virgin, too?"

I got slapped.

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20. Give him the screws

Getting a drink at the bar when all of a sudden, an absurdly tall and extremely hammered albino man shoves his way in to say, "Hi I'm from Kansas and I want to screw you so bad."

My response? "I'd rather not be screwed badly, thanks though."

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19. That's not flirting, just a red flag

I was walking to class, and this guy comes up to me. We proceed to have this conversation:

Creepy Guy: Hi. I've seen you around campus. You're very pretty.

Me: Aw, thanks. I'm [name].

Creepy Guy: I've seen you in the dining hall and walking into the math building and walking out of the math building and getting your hair cut and going into your dorm.

Me: Uh... (walks off really quickly)

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18. What an opening line

I'll tell you the worst way I've tried to flirt with someone.

I was at my local rec center and saw a cute girl sitting by herself, I decided to go over to her and try to start a conversation.

Being the smooth guy that I am I walked up to her and my mind went blank. So I said the first thing that happened to come to my mind which was, "So, do you think Disneyland gets a lot of creepy single guys?"

She let out a forced, awkward laugh, said "yeah" and left.

I'm awful at picking up women.

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17. Jesse's girl

This was two years ago.

My buddy had been talking about this girl he had been hanging with for awhile. He had been taking her out to various venues and just spending time with her, but had not worked up the courage to kiss her. He finally decided to introduce me to her and tells me to meet him at this bar we go to.

I walk in, and he is nowhere in sight, so I text him and he says he is running a little late, he will show up in another hour or so. Crap... So, I start ordering drinks and at the bar I notice this girl who is not bad looking and seems as frustrated as I am. We get to talking about how unreliable people can be, introduce ourselves, and I take her to play a game of pool.

We are flirting pretty hardcore throughout this game, with her "accidentally" brushing up against me and what-not. Eventually I make a bet with her on a shot, if I make it, she owes me a kiss... I sink the shot, make-out with her for a few minutes... yadda yadda yadda, find out it is the girl he has been seeing.

They've been together since, and we didn't inform him of this for a few months...

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16. That's a pretty smooth recovery

My first day at a new high school, I was outside on the quad asking a girl for directions. The next thing I know, I feel a powerful slap on the butt and hear, "Hey Brad!"

I turned around to see a very attractive girl recoil in horror, exclaiming, "You're not Brad!"

Looking her in the eye, I calmly replied, "No, but you can call me Brad if it makes you happy."


15. Friends don't let friends do this

After encouragement, and a few too many drinks, a friend of mine wandered over to a hot chick at a loud party and stumbled into the following exchange:

"Hey! My name's Luis! What's your name?"

"Luis??" She's struggling to hear.

"Haha! Oh wow! Your name's Luis too! That's so crazy!"


"...I'm really hammered. Have a wonderful time." And he wandered off directly into a wall.

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14. Spontaneous rubbing

Oh man. This one burns to relive. About a year and a half ago, I flew into Montana and drove straight to Jackson Hole, Wyoming, with a good buddy of mine. We started drinking pretty heavily at the rodeo, and decided to eventually saddle up at the Million Dollar Cowboy bar.

When we walked in, there was space at the back bar, so we took our positions. Within minutes, we were surrounded by 20 girls from a bachelorette party. Money.

Pause for relevant context: I had been up for about 20 hours off of 3 hours of sleep. I don't have cash, and this is an all cash bar. My buddy, now sitting on my left, is very smooth with girls, and I was in the middle of a dry spell.

One of the girls comes up and sits down on my right, chatting me up. She's gorgeous, and I'm pumped.

After a few minutes, my buddy starts rubbing my leg. I'm a little confused, but figured he was giving me a "hint", and start mirroring his behavior by rubbing the girl's leg. After a few more minutes, he starts rubbing more vigorously. I'm thinking to myself, "this actually works?" But nevertheless I start rubbing her leg more vigorously.

The conversation quickly deteriorates, and she runs off in a hurry to join her friends on the dance floor. I turn to my buddy and he says, "take the f-ing 20!" "What 20?" "The $20 I'm rubbing on your leg so you can buy her a drink!"

She came back 5 minutes later wearing a wedding ring. I'm positive she wasn't married, just applying some creep repellent.

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13. This kid's got stones

When I was 15, a 13-year-old boy came up to me and offered to show me his rock collection. Then he asked if he could see my boobs. I politely declined the latter request but the rock collection was pretty cool.

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12. The straight and narrow

It happened in the smoking room of a hospital (yeah, a smoking room in a was some time ago). A gay nurse (I'm straight) was being super aggressive with his flirting. I would normally just be flattered, but this guy wouldn't let up. I didn't want to be rude, but I also didn't want to lead him on, so I can just sat and nodded as I finished my smoke.

The next day was even more awkward. He apparently realized that I was straight and wasn't comfortable with his advances, so he pretended to be straight, and it was kind of hilarious. He just kept going on about all the straight adult content he consumed. It's like he wanted me to think he was straight but also had no idea how straight guys talk to each other (did he have no straight friends?).

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11. Hungry and humiliated

I used to work at the mall, and many days we would go to a certain burrito place for lunch. None of us employees knew the cute hispanic girls who worked there.

There was one girl there I thought was especially cute, so I decided "by God, I'm going to ask her out!" So I went to the taqueria in question and, when she asked me what I wanted on my burrito, I asked for her number. Since that wasn't a burrito topping, she paused, and then repeated the question.

I looked around. There was a line of hungry, impatient people behind me. Staring, unamused. My momentum was gone. I mumbled something under my breath about "I've seen you here before" or some crazy embarrassed nonsense. Misinterpreting what I was asking her, she leaned over, pointed helpfully at one of the possible burrito toppings, and said "olives?"

It was at that point that I realized that she did not speak English, beyond the basic vocabulary needed to make a burrito. I relented, and ate my lunch in defeat.

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10. The bad finger

I was pretty innocent at 16 and was flirting with a guy on my swim team. For some reason he was wagging his finger in my face, so I snatched it and moved it towards my face...I dunno, I think I was pretending to bite it, just being feisty. He had this intense look on his face, and as I moved the finger to my mouth I suddenly realized, horrified, what it actually looked like.

I dropped his hand and ran out of the room - we didn't talk for months. I was so embarrassed I didn't even want to see him.

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9. Mr. Charming

I was grocery shopping and my basket contained white wine, cat litter and almond milk. Mr. Charming behind me in line tells me that I must be lonely to be buying only those items and that I can come over and make him dinner. He was very confused by my refusal.

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8. A rejection and a lesson

I had an uncontrollable crush on a gorgeous, tall unaffected guy named Alan my first semester of college. He lived on my floor and couldn't be any less into me. I could tell that I had a snowball's chance with him, but the hormones, they are impossible to ignore.

Being very inexperienced, I thought that creating drama would inspire him to see me as the cute vulnerable stereotype I thought all boys wanted. So I manufactured some reason to need to have a long, emotional talk in the hall and, with what I thought was superb timing, I looked up at him with big, teary eyes, paused for two heartbeats and then lunged at him for a kiss.

He called me on my BS so fast, my head spun. "I knew you were going to do that," he said. "You know I'm not interested in you. What made you think that was going to work?"

It was the first time I'd made a pass at a boy since moving to the city from the boonies and it was the first time I'd been rejected. He did me a favor in a way, though. I never used artifice or stereotypes or created false drama again.

I still wish he had let me kiss him, though.

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7. Free love

My wife had this one prior to meeting me.

"Can I buy you a drink?"

"No thanks I am good."

"You telling me all your good loving is free?"

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6. In a previous lifetime

He told me that we were destined to be together because in several previous lifetimes we'd been forbidden teen lovers in an alternate universe where anime was real. He insisted on calling me by my "true name" (the name of some crappy anime character he liked) and he would even "correct" my school papers with the "true name." He had a notebook full of stories and drawings about our future life together, and he'd picked out names for our children and designed my wedding dress.

To be clear, he showed all of this to me after we'd talked to each other casually a few times in class... We didn't even know one another.

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5. The dude was baby crazy

Maybe not the worst, but certainly the weirdest.

Some guy came up to me at work and started quizzing me. "What's your name?" "Do you have a boyfriend?" "Do you think I'm cute?" The direct approach. I assume it has worked for him in the past.

But then he asked if I had any kids. I said no. This seemed to derail his train of thought completely. He said he couldn't believe it; he'd never met "a girl [my] age" who didn't have kids, and he kept following me around and repeating it. "Seriously? You don't have any kids? You're not messing with me?"

I escaped into the warehouse and didn't come out until I was sure he'd gone.

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4. Unforced errors

I went to Israel as a teenager. towards the beginning of the trip, we had a 5 hour bus ride through the desert. I was pretty sleep deprived already and somehow managed to get the best-looking girl on the trip to sit with me for the ride.

After an hour or so of chatting it up, I decided to take it to the next level and put my arm around her. Surprisingly, she was into it. We both fell asleep like this for around 20 minutes.

We then woke up and she went to take a drink from her 1 liter water bottle. I decide for some completely unknown reason that it would be funny and flirty to squeeze the water out of the bottle. It explodes all over her face and clothes, drenching her. I was almost as surprised as she was.

I instantly apologized for my "joke" and we rode for endless hours through the desert in moist awkward silence. I had blown my chance, obviously.

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3. More like Al Bundy

When I was younger I asked a stranger out on a whim. Surprisingly she says yes and I was going on my first real date ever!

So I pick her up and as we are chatting I get so nervous I take a wrong turn and have to pull into an unlit parking lot and turn around. I apologized for the wrong turn and she just stares me down and tells me not to try anything her family knows where she's at.

Completely shocked I stupidly asked if I really seemed like that kind of guy and she just looked me dead in the eyes and said, "Ted Bundy seemed nice didn't he?".She was completely serious and not joking. Cue the most awkward hour and half movie experience of my life.

I did not get a second date and I strongly suggest men and women avoid any mentions of murder on dates.

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2. We've all been there

Oh, man.

Once in 6th grade, I was sitting in class when I noticed the girl I had a massive crush on sticking her tongue out at me in a playful way from across the room. Well, I took this as an invitation to reciprocate. Back and forth, we traded silly faces. That moment may have been the greatest of my entire childhood had it not been followed by the worst.

I felt a tap on my shoulder, and spun around to see the guy who made my life a living nightmare (tall, good-looking, captain of the basketball team, bullied me constantly) looking at me like I had just slapped his dog. Apparently, she had been trading looks with him, and I was caught in the cross-fire. Yeah, that one still stings.

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1. The waitress serves it up

Went to this bar at an outdoor strip mall with my brother, I work a very odd schedule so I was off, and my girlfriend had the car, so he picked me up on his lunch break. So we could Grab a bite, catch up. That sort of thing.

This waitress is way way younger than us (I'm in my 30's, my brother is in his 40's) seriously this girl couldn't have been older than 18.

Very flirty. She complimented my beard, and my tattoos, made a lot of effort to stay near our table and join in on our conversation. My brother was cracking up, and texting our younger brothers about it, they're telling me "go for it" and just being jerks.

We get done with lunch, cash out and leave.

My brother comes back with his wife a few days later, the same waitress was there and recognized him. So she waited their table. She asked him who I was, and how he knew me, explained I was his brother and she asked what my name was. She also told him I was "dreamy"

Now my first name is John. I also have a very generic last name. My brother said he just said my first name, but his work jacket has his full name on it. So next thing I know, I have a friend request on a certain social media. How she found me with a combo of my generic ass name and no mutual friends I'll never know.

Before leaving she brought out the same thing I ordered the other day, and told him it was on the house and to take it in case "John gets hungry"

So before this could escalate any further and get anymore weird I decided to tell my SO, she laughed so hard.

We're going there this Wednesday when I'm off because she wants to see this girl who has become enamored with me.

Wish me luck.

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