Have you ever said something regrettable to a love interest, only to be pleasantly surprised by their reaction? Here, people share their worst attempt at hitting on someone that actually worked.
1. I drunkenly texted the complete lyrics of Baby Got Back to a girl.
It went ok…we got married.
Fishsound
2. My Dad’s pickup line to my Mum was, “Nice legs… Shame about the face.”
Fergatron
3. At a bar. Saw a guy that was super cute. I couldn’t get his attention since he was sitting at the bar facing away from me. From across the room, I threw my lighter as hard as I could and hit him directly and forcefully in the back of the head. As he was nursing his newly forming whelp, I sauntered across the room towards him, with a big smile, and said, “I think I dropped my lighter.”
Nine years later and he still has a little bump on hey he back of his head.
Auntmarge
4. Pulled up to a red light. Car next to me is being driven by a girl from school (I was sixteen/seventeen) that I hadn’t seen in a few months. I liked her but she’d been dating some other guy at the time so I’d never pursued her. However a mutual friend told me she’d been dumped a short while earlier.
Both of our windows were down. I ask her if she wants to race. She laughs and asks what are we going to bet. I said loser has to take the winner to dinner and a movie. She agreed. Light turns green and she’s off like a flash.
I slowly ease off the line after the police officer that was behind me takes off after her. I swear I never saw him there.
Officer pulls her over and she ends up with a ticket for “Show of Acceleration” or some other political term for drag racing; but we still went out on a few dates. Saw Gattaca with her, which was neat.
FunDirector
5. Twas Halloween night and I was dressed as a cat and she was dressed as a cat , I said lets go make Kittens. It worked.
Thestagrabbit
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6. Halloween night 2012. Went up to a girl that I thought was dressed as an apple and said “You’re the apple of my eye”.
“I’m a strawberry” she replied.
“Okay well, you’re the strawberry of my eye”.
Next thing I know we are at her apartment.
Travvers
7. I wasn’t hitting on him, but once a guy brought in his little daughter to eat at the restaurant I used to serve at and during the 20-odd minutes they were there I
– Spilled Coke all over him
– Knocked over his daughter’s orange juice while trying to clean up the Coke
– brought out the wrong appetizer
– Forgot to give them silverware to eat the appetizer they didn’t order
– Forgot to punch in their order so when their food did come out it was extremely late
– Dropped a ramekin of Ranch dressing on the guy’s lap before he had even started eating, ruining his trousers to the point that he asked me to just bag up their food so they could take it to-go
– Somehow misplaced $5 of his change and was too embarrassed to go to my manager after all my other screw-ups so I just gave the guy $5 out of my own wallet and ran away to the bathroom nearly in tears from frustration.
When I went back to clear the table after they had gone he had left the $5 I had given him and a $20 tip on top of it and a note with his number on it that said, “We all have bad days. Give me a call.”
Shark-Farts
8. Gave my crush a stuffed animal duck in 8th grade, and said “I wanna duck you.”
ROFL_COPTER_EXTREME
9. My buddy asked a waitress at Red Lobster, “So… do you come here often?” and got her number.
[deleted]
10. I once picked up a girl from a bar who kept acting uncomfortable about going home.
She told me she wasn’t comfortable being a one night stand.
I said, “You don’t have to be, we can bang in the morning too.”
Then we banged.
AsianThunder
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11. Back in high school my best friend Bob and I went to a concert at a local coffee shop one weekend. While we were there we saw these two girls (let’s call them Emily and Laura) hanging out together and started talking to them, flirting and such. My friend has his eye on Laura, but every time he talks to her he calls her by the wrong name, and she corrects him:
B: Liz, you’ll love this one.
L: My name is Laura.
B: Oh yeah, sorry…
This goes on for the next couple of hours, with different names from Bob and growing exasperation from Laura. Finally, as they’re getting ready to leave, they have one final exchange:
B: Well Mary, it was great to meet you.
L: SIGH My name is LAURA!
B: I’m so sorry. The thing is, I’m much better at remembering names when they go with numbers.
That guy had for that line for hours, and I’ll be damned if it didn’t work.
Shepdaddy
12. I was taking to this girl at a bar and I said, “There’s a TV program I want to watch, let’s go to a hotel”
She came along.
When we got there she asked “what show is it?”
I said ” what show? you know what this is about”
Then we were bangin’
Banged for a good long while.
[deleted]
13. Girl: Hi. Have we met before?
Me: No.
Girl: I’m Tabby… like the cat.
Shake hands
Me: I’m Taylor.
Girl: OH! That’s my brother’s name!
Me: Well that will be awkward when we get married.
We’ve been dating for 6 1/2 years now.
The_Holy_Pope
14. “I see you’re drinking one percent. Is that ’cause you think you’re fat? ‘Cause you’re not. You could be drinking whole if you wanted to.”
King_Loner
15. Back in college I would flirt by playing what I called “the middle name game.” Basically, if I’m chatting a girl up and things are going well, I’d playfully bet her a kiss that I could guess her middle name in three guesses. The first time I tried this I was just thinking ,”What the hell, why not?”
Well the Middle Name Game ended up working perfectly for a few reasons: Every girl has one of four middle names: Anne, Marie, Elizabeth, or Rose. The odds are definitely in my favor for getting it. I’d be subtle, making a show of thinking about what I’d guess next, and I’d get it right like 90% of the time.
But the best part is that the game is an astoundingly good test of how attractive the girl in question found me. Occasionally they’d be weirded out and decline, which is easy enough to shrug off, but a majority of the time they’d go along with it. And if she’s going along with it, she wants to make out with you, so it doesn’t really matter if you guess correctly.
Once I couldn’t guess after three tries, shrugged and said, “That’s a shame, I’m a pretty good kisser.” The girl responded, “Prove it.”
I suppose the idea of a kiss/make out bet could be applied to anything, but middle names are a fun and innocuous topic.
IAmAlpharius
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16. “My friends think we’d be cute together.”
Two years of my life.
[deleted]
17. I asked out my first girlfriend by simply saying, “I like you. Want to go get a pizza Saturday?”
I can be a very blunt person.
IHateAnvils
18. Some girls in college made a bowl of “Rummy Bears” (let gummy bears soak in rum overnight) for a house party. During the party, I grabbed a handful of the bears from the bowl, then asked a random chick if she wanted some Rummy Bears. She said yes, so I tossed a handful in my mouth then proceeded to make out with her. Fun night and best, successful pick-up line I’ve ever had.
MyNameIsntPatrick
19. I met the woman who would be my eventual wife when I was about 5 years old. I literally hit her with a stick in the park that day. She ran home crying. I still hear about it
Lurkalo
20. I had a friend who picked up his long term girlfriend at the bar using the line, “I can’t wait to disappoint you sexually.”
Neonappa
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21. I drunk texted this girl I thought was way out of my league that I wouldn’t sleep with her until she made an honest man out of me and took me to Olive Garden.
Went to Olive Garden, slept together, dated for six months, met her parents. Split up because she didn’t have a personality.
[deleted]
22. I tried a Futurama line and it worked to start up a conversation. “Hi, I’m nomoregaming. My two favorite things are commitment and changing myself.”
nomoregaming
23. She used the cheesiest line in the book, and I’d been saving up a response for it for years (heard it from a comedian once):
Her: “What’s your sign?”
Me: “Stop.”
Luckily, she had a really great sense of humor, and we dated for about a year after that.
80sflounder
24. Asked a girl if she was a pirate would she want a parrot on this shoulder (the one closest to me) or this shoulder (the one furthest from me, putting my arm around her), got a date out of it.
Granted we were flirting with one another pretty hard, so it probably would’ve happened without that cheesy pickup line.
chance__
25. I was eating dinner with a large group friends at a Baker’s Square and when my group got up to leave, I told the chick across from me, “See ya later, Sweet Tits.”
Make-outs later occurred with Sweet Tits.
My_Empty_Wallet
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26. After a number of failed club trips with a friend, we took an unplanned night out. Both of is ended up wrecked, and decided we were going to pretend to be Australian for the rest of the night (we live in Scotland).
So we trolled around the nightclub asking various females if they were “Good Scottish girls” in a horrendous accent. One of them ended up practically fainted with excitement due to meeting two ‘Australians’ .
This was great banter until she proclaimed, ” Here are my other Australian friends” at which point my mate screamed, “BAIL!!” and we both ran away giggling.
Adamczuk
27. We were talking about sports, and I wasn’t actually hitting on him, but was joking with him about how much I hate sports commentators. I didn’t know he was a sports commentator.
Totosmaster
28. Junior year of high school. I had just been dumped, and a cute girl I’d liked for a while was sitting in front of me. I kept badgering her and she constantly told me to be quiet because the teacher would notice. She was a Hermione type. When the teacher eventually called me out, I declared I couldn’t be quiet until she agreed to marry me.
“Well? What’s the verdict? Because I’d like to continue my lesson” said the teacher, completely uncharacteristic of his usual strict self. With the whole class watching, she grew red as a beet and said, “Okay…” In the most defeated tone I’ve ever heard. We dated three years, have been married five years, and now have two adorable kids.. Nailed it.
[deleted]
29. I was majorly sleep deprived. Hadn’t slept in something like 30 hours. Some friends of my roommate came to visit. I wanted to go to sleep, but because there was this “mini-party” of sorts going on just outside my bedroom I figured I’d join in. Not like I’d be getting any sleep anyway, what with all that racket.
We all congregated in the kitchen, having drinks and chatting. I was leaning against the counter. I was standing, my eyes were open, but I was asleep for all intents and purposes.
A couple minutes in I realized I had been staring at this girl’s heaving, exposed cleavage. I mean just… glaring… openly… in the middle of a group in a brightly-lit kitchen… and I had been doing it for at least a minute and a half without even realizing it.
My natural reaction was to correct myself by looking away. But what do you do whenever you catch yourself staring? You first look at the person you were staring at to see if they noticed. It’s instinctive, right? Well, I tilted my vision up just a bit and sure enough, she was glaring right back at me. It was clear that she was long past the “oh I caught you looking” phase, even past the “holy crap, are you really going to stare at my tits right in front of everybody?” phase. No, the look in her eyes said that she was well into the confusion and acceptance phase. Her look said: “You’ve been staring for so long, and so fearlessly, that I don’t know how I should feel.” If I had been staring less she would have thought I was just being a creep, but the fact that I was so shameless (or, in reality, oblivious) about it meant that she didn’t know what to think.
Normally I would feel horrified. But instead my brain was working so slowly that by the time I started to feel the pinch of guilt I realized that I had been staring even longer, only this time, directly into her gawking, confused eyes. That’s when she looked away. It was like I had won a staring contest without even trying.
Again, normally I would feel bad about this, worried I was making her uncomfortable or something, but I wasn’t playing with a full deck.
So I finished my drink and announced I was going to bed, thinking that was the end of that.
Instead, a week later, she came over again, only this time I was fully conscious and fully sober. I will spare you the finer, filthier details, but let’s just say the hookup was immediate and it was fierce.
I got the impression that our first encounter had been so strange to her that she became fixated on trying to figure out who this weird guy was that would do something so audacious. It was the one time in my life when I felt like I got to be that guy, and it worked, only completely without my conscious input.
10tothe24th
30. “This bible passage was really interesting, let’s discuss it together.” College Christian group had some really nice girls in it.
And then later “this path is really slippery, want to hold hands?”
And then even later “I think I have something in my eye, can you check?”
Can’t believe those worked.
Kukulkun
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31. I asked a Japanese girl to teach me some Japanese phrases and words, like “do you like this” or “I like that” etc. So a couple “dates” later, pretending to learn more Japanese I just said “I like you” in Japanese. She said she liked me too. 4 years later, we got married.
Mr_chanderson
32. I had a guy hitting on me at a pub, and would not give up. I put my arm around a girl while he was getting a drink, and begged her to act like my girlfriend to get this guy to leave me alone. He was persistent, and I didn’t feel like getting in a fight.
Well, we talked for awhile, and I took her out to dinner the next night; partly to say thank-you, and partly because she was gorgeous, and we seemed to hit it off.
17 years later, she has been my wife for 15 years.
Renob151
33. Attempted to chat up one of the groomsmen at my cousin’s wedding. I was hammered, and I believe it went something like “So… I hear you used to date my cousin.” This was followed by horrible drunken flirting in front of my family and some woman he’d hooked up with, who was not happy.
Smooth.
Worked, though.
MetalSpider
34. “Sir, would you date me? If you say no I was just kidding.”
First time I outright hit on someone. After 7 years, we are now engaged to be married.
Tea_bird
35. I was in a club and a girl was staring at me. Being the jerk that I am, I looked at her and said, “Is there a dildo stuck to my head or is there some reason youre looking at me?” It went from there. Felt bad for saying it but it worked.
Sonicisreal