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Flirting With Disaster: Readers Share Their Worst Flirting Failures

People generally fall into two categories when it comes to flirting, either you have the confidence to do it, or you don’t. However, flirting can sometimes take an unfortunate turn, leading to cringe-worthy moments. From awkward pick-up lines to embarrassing blunders, we’ve all had our fair share of horrible flirting experiences.

The Awkward Part

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One poster shared, “Just this morning, I’m in line to order at Starbucks. The guy in front of me orders, and the barista 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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A second poster added, “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 leaped 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.”

Finger Guns

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A third poster commented, “I was talking to a girl in the elevator of my faculty. I asked her name as I raised my hand to make a finger gun gesture. The space was so small I ended up touching her boobs with it. I’m a moron.”.

Ginger Mania

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This user said, “When I was in college, I had long hair, and I’m also a redhead, so it was quite a mane. One brutally cold day, I was wearing a long black overcoat while pumping gas, and I heard a voice behind me said, “Hey baby, want to go back to my place to get warm?”. I turned around, thinking it must have been directed at someone else, but instead saw the most surprised old man I’d ever seen. When he caught sight of my full beard, he jumped like he just touched a live wire. He stammered, “Ohh.. god bless you… ohh… god bless you… ” as he backpedaled back to his pickup truck, then ran over a curb trying to leave the gas station.”


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A Redditor added, “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 hell looking at me like I had just killed his dog. Apparently, she had been trading looks with him, and I was caught in the crossfire. Yeah, that one still stings.”

Dump Day

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A user recalled, “In high school, I sat beside my crush. I looked over and saw that her pencil read, “Wednesday is hump day!” My heart almost burst out of my mouth. What day is it? Oh my god, it’s Tuesday! It wasn’t until much later that I learned “hump day” didn’t mean “the day Heather humps everyone indiscriminately.”

Manufactured Drama

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One poster commented, “I had an uncontrollable crush on a gorgeous, tall unaffected guy named Alan my first semester of college. 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 lunged at him for a kiss. He called me on my sh****t so fast my head spun.”

Awkward Hugs

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This Redditor stated, “I knew a girl in college who I suspected was into me. She confirmed it, finally, in the third year, by saying, “If you got drunk, I would take advantage of you” (I don’t drink). Every time I saw her, and she was drunk, she would want to hug me, and they were these long, unrelenting hugs where she’d lean slightly back (She was very short) and look into my eyes as long as she could, with her face as close as possible. I had to keep looking away because I suspected if I’d maintained eye contact too long, she’d lean in for a kiss or something.”

Snot What He Wanted

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One user added, “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.”

Did Her A Favor

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A Redditor mentioned, “I met this gorgeous girl who worked in a bookshop. I told her I liked her almost immediately after speaking to her. She says she won’t date me until she knows me better and that it is OK for me to stop at the bookshop and have a chat whenever I feel like it. We do this a few times. One afternoon her boss is working behind her, but she tells me it was OK to chat. After a while, her boss comes to me and tells me to leave. I returned to the shop after a few days, and only the boss is there. I apologize for the incident, and she tells me that she’s fired the girl I liked and that I did her a favor for giving her a reason to fire her.”

Language Barrier

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A user said, “I used to work at the mall and often went to a burrito place for lunch. There was one girl there I thought was especially cute, so I decided I’m going to ask her out! I went to the taqueria, 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 repeated the question. Embarrassed, I asked a second time for her number. Misinterpreting what I asked her, she leaned over and pointed helpfully at one of the possible burrito toppings. 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.”

This Burned

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This poster shared, “I burn like you wouldn’t believe in the sun. When I visited San Diego for the first time, I walked all over without sunscreen. My face was swollen and peeling, but I forgot about it because I was really drunk. We were out at the bars, and I was talking to this cute girl, thinking I was being devastatingly charming, and she stops me and says, “I don’t mean to stop you, and you seem like a really nice guy but do you need to go to the hospital? Your face is really swollen”. Devastating.”

Relate To Being Related

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A top-liked comment said, “Realizing that I was related to the girl I was flirting with…and then realizing that she didn’t care we were related….”

Didn’t Get The Hint

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This user commented, “When I was in high school, I asked a girl I liked (and thought was into me) what she was doing one night, and she responded that her mom was not home. Being completely oblivious to the hint, I responded, “And your dad?”  She responded that he had died some years ago.. and never spoke to her again.”

Stepping On Toes

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This Redditor shared, “There was this cute hippie girl who I had an absolutely massive crush on. We’d been talking for a little while, and things were looking positive. So, myself and a group of friends went to meet her and her group of people in a park. Get there, everybody’s greeting one another, and she and I kind of drift together to do a little “greet with a hug” thing. She was wearing Birkenstocks. I step in to give her a hug and kick her big toenail clean off. Completely off.”

Stark Raving Frozen

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This poster added, “As a raver, we would all go out and visit this dirty club where pretty much anything went (no bar). So I see this rather hot girl on a staircase, and I was pretty fubar by this point. I’m like, “Hey, how you doing?” we talk for a minute or so, then I just throw in the question, “So hey, are you single?” she goes, “Yeah,” then I just freeze up, say nothing and stand there. After 30 secs or so, she just goes, “Well, this is awkward,” and walks off. It still haunts me to this day!”

Very Cute, Very Married

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One user said, “Friends of mine threw a Halloween party. I decide to take a little break and sit by myself by the fire and have a smoke. A girl comes over, very cute, very friendly, very flirty. So we sit there and talk and flirt for like a half hour. Then some dude walks up, “Oh hey, this is my husband…”

Overly Playful

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A Redditor added, “I’m a waiter at a fine dining restaurant. I often flirt playfully with female patrons. The other night I’m waiting on a senior couple and their friend whom they’d taken out for her birthday. During the night, I discover that the couple’s friend is having a horrible week and seemed lonely. I up my game a little bit and flirt/compliment her a few times through dinner. After they’ve eaten, the couple orders a slice of cheesecake, but their friend declines, sort of sadly, attempting to cheer her up. I say, “That’s too bad. I have a special dessert in mind for you.” I wink at her and walk away before the full implications of what I’d just said struck me.”

Future Plans

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A top liked-comment said, “I was dancing with this guy at a club, and we talked. He asks me a few questions about college and then goes, “So, what are you doing after?” I interpret this as meaning he wants to return to his place, so I say, “Sorry, I’m with my friends tonight.” He starts to laugh and says, “No, I meant, what are you doing after college? I turned beet red, mumbled something unintelligible, and kept dancing. After a few minutes of silence, I made an excuse and walked away.”

Not Right Now

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This Redditor recalled, “I asked a girl to prom, and my suave friend was giving me advice. He said that beforehand I should call her and talk to her a bit and ask what she was wearing. Later, I found out that he meant the day of the prom’ as opposed to “right now.”

Not For Her

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Finally, a Redditor shared, “We were downtown at a bar. Now, I don’t normally go out of my way to flirt/hit on chicks, but there was this one gal… she wasn’t “hot,” but man, she was exactly my type and obviously the kind of person I really, really wanted to talk to. So I walk over and introduce myself to her, feeling more confident than I ever have in similar situations. She responds warmly but directs my attention to the girl standing next to her. “Sorry, you’re really nice, and I like you, but this is my girlfriend.” Broke my heart.”

Source: Redditors

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