32 Hilariously Embarrassing Attempts at Flirting

‘How much do you weigh?’
32 Hilariously Embarrassing Attempts at Flirting

Flirting is one of the most humiliating things you can do. You pretty much never know if your attempt is going to land. In fact, you’re guaranteed rejection more often than not, and some rejections are a fate worse than death. Sure you’re alive, but just barely. Take, for example, the guy who spent $500 on scotch for the entire bar, all for the purpose of impressing a girl there. Not only did he not impress said girl, but he got blackout drunk and had to retrace his steps the next morning to find all of his belongings — and that isn’t even the most mortifying story below. 

Redditors have reached into the crevices of their mind to pull out their most embarrassing attempts at flirting, and all we can say is, don’t try this at home. Like really, don’t. You will not be getting laid if you tell a girl you want to fight crime together.

. 9y One time I got drunk at a bar and started to pretend that I was fishing for girls. Didn't catch anything that night. Bartender said I was using bad bait. ... 537
CakeToPersonRatio . . 12y I told a girl she would look good even with a bag over her head. I honestly thought it was a good line until I noticed the face she was making. ... 150
 . 12y 9th grade or so. I was incapable of talking in any reasonable way to good looking girls. I had decided that the way to make myself attractive to them was by being so offputting that they'd have to take notice. At a friend's pool party, a pretty fresh-faced girl struck up some chatter. I proceeded to baselessly insult her before quickly jumping backwards into the pool fully clothed with shoes on. When my head poked back out of the water she had moved the hell on just like any self- respecting person would. I was such a
 • 9y Unfortunately me. So, I was hitting on this girl and she called herself fat. I decided it would be a good idea to ask how much she weighs. The look on her face told me to give up forever. ... 805
francescj 13y I was talking to a girl in the elevator of my faculty, I asked her name as I was raising my hand to make a finger gun gesture. The space was so small I ended up touching her tits with it. ... 206
prettydumb1 . 1 12y When I was in 3rd grade during outdoor soccer every time I was near her I pretended to be a Goliath from StarCraft.. Yeah.. ... 306
Vijchti . . 12y I tried to pick up a box of Capri Sun with one hand. ... 855
 12y I bought and sent myself roses on Valentine's day, in order to convince the girls in my 10th grade class that I had admirers. Everybody just thought of me as the creepy guy who bought himself flowers. ... 532
 12y There was this hot girl in 7th grade, and she always commented on how she loved my eyes. So whenever I was around her I tried to stand almost directly in the sun so it shone off my beautiful retinas. Never worked. ... 337
CrackTheSkye 12y Spent an entire paycheck (around $500 at the time, I seem to recall) on scotch (for the entire bar) in an effort to impress some girl there. Instead, I blacked out. The next day, I woke up in my friend's basement missing my shirt, my socks, one shoe, my keys, my wallet, and my cellphone. Retracing my steps, my shirt was on the front lawn. Socks were in the back of the truck I was hauled into to get me home. Shoe was in front of the bar. Keys were in the possession of the hot girl I
vapulate. 12y i slipped $5 in her locker taped to a note expressing my love for her. this was in 9th grade ... 163
meatu5 . 9y A girl and I were washing dishes at work. Suddenly our hands touched, to which I felt compelled to say: our hands touched. She then replied: yep. They did. ... 956
strongo . . 12y I walked slower in front of some girls once... noticeably slower...it was uncomfortable for all parties...Then I sped up and left and it was only then uncomfortable for me. ... 559
MinervaDreaming . 12y Oh god, it was painful to remember this. I think I was 10? I wrote a letter to a girl then went around my house and found as much spare change as I could. I stuck all of this change to a long strip of scotch tape, and stuck it in the envelope with the letter. Gave it to her the next day. I honestly have no recollection of what followed - probably blocking out the trauma. ... 594
 . 12y When I was 12 or so, I decided I wanted to flirt with a boy. Unfortunately, all I'd heard about flirting at that stage was that it involved lots of eye contact. I must have eye-laser stared that boy down for a solid hour or so. ... 865
caparza. 9y What's the difference between a Corvette and a boner? I don't have a Corvette!
 12y I gave a guy my little carton of chocolate milk at lunch. Sad part was we were in our mid-twenties. ... 231
browwiw . 13y Realizing that I was related to the girl I was flirting with...and then realizing that she didn't care we were related... ... 83
skippy17 . 13y My failed flirting attempts usually involve girls not recognizing sarcasm. The favorite of these is, in response to her mentioning she was taking a class in race relations (or something like that), I reply, That's interesting, I'm actually racist myself. Her eyes got real big and she got real quiet, Are you serious? ... 913
bigroblee . . 12y I gave a girl I liked in seventh grade an apple. She was not impressed. ... 238
majorpenalty . 1 13y 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. ... 669
mileylols . . 12y I bought her a flower every day for two weeks. It seemed like a good idea at the time. ... 289
ju2tin . 12y Was working out in our dorm gym when two hot girls came in to do their workouts. I took off my shirt and continued with my workout, like it was just something I do normally. For some reason, I thought the sight of my completely non-ripped, ordinary-looking shirtless torso would make them realize that, yes, they wanted me, and taking my shirt off was in no way a creepy and pathetic ploy. ... 239
missingsf 9y It was me. And it was humiliating. I was in my early 30's and had just moved to a new town. I didn't know anyone, so I decided to go watch some football games at a local sports bar. Apparently I was a little overserved because I found the 21 year old bartender very attractive but couldn't speak without slurring my words. So I decided to ask her for a napkin. (Grunt at her was more like it.) On this napkin I wrote something about wanting to explore this new city with her and then kind of shoved
Solarscout . 12y I was in junior high school, and the girl in question's locker was right next to mine. And every day, she tried to start a conversation with me, and to my eternal chagrin, I decided everyday to not answer and just look back blankly, assuming that that was clearly the prime way to flirt. Needless to say she hates me now. ... 351
BlackBen . . 12y When I was 11 I used to challenge other guys to race me in a sprint across the playground. I was fast and I'd always win. Figured that would impress them... ... 189
cudne1am . 12y Not too long ago at a party, I was trying to impress a guy so I put a can of sparks in my cleavage and drank out of it with no hands... ... 451
Golden_orb . 1 12y At a bar: Can I sploosh around in your junk with my junk. I got a no :( ... 56
 . 12y When I was 14 I was at the local mall waiting to cross the street. Some really attractive girls about my age were on the other side, so I casually tried to tap the pedestrian cross button. I ended up slamming it with the side of my hand, breaking my hand in the process trying to look cool (it was a weird design). Had to get my mom to come grab me and take me to the doctor... talk about awkward. ... 346
ZoneGuy0. 12y Anything I've done to impress a girl ever. In high school I once made a song in Fruity Loops for a girl and gave her a CD of it. Pathetic and creepy. Also, it seems that my encyclopedic knowledge of the Twilight Zone doesn't seem to attract women at all. Imagine that. ... 359
 . 12y Early in high school, I was keen on the girl that sat behind me. She really liked Hershey Kisses (I mean really liked them; she would have some almost everyday), so one day I bought a big bag with the intentions of giving it to her. I turned around in class the next day and put the bag in front of her on her desk. She said, I don't want those. Shit. Immediate redface. I responded, Uh, I know. I was just showing you I had them. She totally believed me. ... 239
Kuothe . . 13y Hey, do you have plans tonight? No, my mom's not home And your dad? .. Не died some years ago.. got drunk, fainted and hit his head with a table and died. Oh... ... 75
Scroll down for the next article
Forgot Password?