What Was Your Worst "Flirting Fail" Experience?

Question

What Was Your Worst "Flirting Fail" Experience?

ChrisMaster69 · Accepted Answer

Fuck I have crashed and burned more times than I can count.

Couple of my worst.

a nun, hey I thought they wore nun outfits all the time and simply upping your game when they actually tell you they are a nun also does not work, so a bit of a double fail. Annoyingly she was pretty and a redhead and Irish.

I've flirted with my bosses wife before and ‘failed’ when he walked over, telling him to find his own skirt really was not the best idea, it was a rather interesting chat in the morning, to be fair she was flirting back and lovely boobs.

there is a huge list that includes lesbians (girls that suddenly became lesbian once I chatted to them), barmaids, girls that simply do not understand English (never mind geordie).

the list is seriously long, but nothing ventured nothing gained.

InventorofWarp · Accepted Answer

Her: "So, where are we going?"
Me after picking her up for the coming date while driving: "Oh, I was thinking I'd take you out to the woods really deep in the forest where no one could hear you scream and put some of the duct tape I have to good use."
Her: ...
And that was the story of Michelle, who I never saw again.

In my defense, the lady I currently fancy has a sense of humour just as fucking sick as mine and that same line killed on her (haha, literally!). She even threw me for a gaff by throwing in a line about chloryphorm.

HHHHIHHHHHIHHHH · Accepted Answer

My flirting was giving a long look (with probably killer eye, I have sometimes this kind of intense eye expression) at my crush who I was very attracted to and it was a little uncomfirtable feeling for me because i didn't know him and didn't know how to get to know him and was pissed off by the fact how hard low is my chance to get him interested in me (I was and still a little am insecure), so I was just looking into his eyes, and this look was crawling up on my face so much so that he started to probably feel a little disturbed by me in the end

Anonymous · Accepted Answer

I start suble and I am ok good at telling when a man is interested or not, so not so bad when I attempted. Worst were the times when it turned out the guy liked the flirting but had neglected to tell he had a girlfriend. Like one did not tell me until a month of building up a relation, and others not until I would go for a kiss.
The other way around I experienced worse.. many drunks who would not accept a no, and I remember a guy who started talking to me about the most famous male porn star. He even wanted to show me some clips xD

AndrewMG · Answer

I can probably narrow it down to a top ten! lol
1. The time I pulled a lass, spent the night at her house then in the morning went to the local shop to buy breakfast and forgot where she lived (I'd not taken my mobile with me) and ended up walking into a strangers house armed with milk and bacon.
2. The time I booked tickets to go to festival with a girl I was dating, we brought the tickets 3 months before the festival and then split up a few days before the festival, but both decided to attend out of stubbornness and the fact we couldn't get a refund.. so 3 days spent in a tent together in which time she invited an old boyfriend and I spent my time trying to find alternative accommodation whilst on the pull and essentially taking advantage of the mass availability of alcohol and weed lol

So that's 2... There's far more stories in the top 10 though lol

MasterOfReality · Answer

A few years ago... I was standing at the beer aisle section trying to make a choice and I saw this hot girl walk up beside me. She gave me a nice smile and then turned to look at the choices. My mind was racing to come up with something to say to her when all of a sudden she said “So what are you doing tonight?” Shocked, I was like, “Uh, I don’t really have any real plans.. How about you?” She paused and said “you wanna hang out and drink a few beers with me?” Elated, I said “Sure! You wanna go out some place or,...” and that’s when she interrupted with, “Hang on a second, some guy in the store is asking me something.”
She was on a blue tooth call...

Lliam · Answer

In junior high, with the first girl I had ever been alone with, we were kissing (and I was doing it badly). But I kept trying to sneak my fingers down the front of her blouse. She kept pushing them away. She finally stormed off and we never talked again. Yeah, I was being super creepy because I had no idea what to do. I'm laughing thinking about it. What a dork.

PaynefulPleasures · Answer

I've had a few in my younger years, I think the worst was when I thought the person calling was this guy I was so into before cell phones land line anyways I don't remember every detail but it was this guys Dad letting me know that his son had to work & would call me later. I was so embarrassed 😳

loves2learn · Answer

Omg! The serial killer one!!! True story! 🤣🤣🤣🤣

I tried to flirt and ended up talking about serial killers. My favorite serial killer is Ted Bundy (as in I find him fascinating, what he did was horrific). He was so handsome (for the time) and had an amazing girlfriend. Could have had any woman he wanted. Yet be brutally raped and murdered women. M

There I go again...😬

cheapshotbob · Answer

it was kind of a me thinking the flirting was with me , was in church once when i was little and this cute girl was smiling and stuff and she waved at me and i waved back
she looked the other way when i did. after church i asked why she waved and smiled etc. she said it was for the boy behind me... that was my worst fail but i doubt it can get worse lol

courtney06 · Answer

I was shopping and the sales guy came on to me. I gave him my number and really thought he was going to contact me. I never heard from him so I went to the store about a day or so later and asked him what happened. He said he threw the number out because he already has a girlfriend. So he only hit on me to get me to buy something. What a slap in the face. I ended up returning what I purchased and bought the same thing cheaper online.

Sensmind · Answer

Haha Everyone must have this and the older you get , the more of them - Back in the days of a disco in my school, (I think it was in black and white, joking) - Anyway I worked up the courage to ask a girl to start dating and things were going along swimingly for about 20 minutes till we both realised she thought I was being a wingman for another guy she liked - Embarrassment all around and to compound it, she came to me a few weeks later to ask me out and I was too embarrassed to say "Yes"

Anonymous · Answer

I'm naturally flirty without any intention.

One cute guy came to me at work and I helped him then we chatted a bit in a smooth way.

He mentioned that he is living in another far area and I said excitedly that I loved that place and would love to move there one day.

He wasted no time and asked for my number.

I'm married... I apologized then
we had this awkward silence and he left lol.

Kayla45 · Answer

I attempted to flirt with a guy on highschool that I really liked for a long time, we chatted and had a little fun teasing each other. Eventually I got the courage to ask him out but in the process I accidentally snorted out of my nose like a little piggy and ran away embarrassed after that.

I consider that to be a major fail on my part.

Ironic_Method · Answer

There have been a few times where some really cute girls have obviously flirted with me, but I didn't realize it until I was telling someone else about "this weird interaction" I had earlier.

I'd like to think Im not as dense now, but...

invalid1 · Answer

I like the memes 😂👌
Well for me, I think I am a little bit insecure so I think if I flirt they will think I am creep.

Plus tbh, you never know with girls.
they're like "yes but no", "be polite but be confident", "flirt but don't flirt", "want me but don't need me". It becomes so hard to navigate until now they're all my sisters lol

GoodGuyBreakingBad · Answer

I wrote a love letter to this girl named Sandy, my sister gave her the letter
but here Sandy was dating a guy and she wrote back a real sarcastic letter
back to me stating Sandy Loves Steve and wow that taught me that
flirting can lead to something else and I would always check her out
never figured she was with a guy, well to this day I think Sandy ended
up Single and her hair was long grey and white not taking care of herself

Newgee123 · Answer

I'm always terrible at it..
I always forget to say 'The right things' and just try to use the new friend route and it never works.

The one time i actually got a date out of it, i was a bit tipsy..

Otherwise, i get too nervous and try to leave

Tunasub · Answer

Flirting With you Brains... lol major fail I'd say. Hurt my feeling.. I only have one.(feeling)

Seriously I've had a few. some people just don't know how to flirt... and it totally just fucks up the whole situation. Maybe it's me but I always end up explaining that I was just teasing..

Avicenna · Answer

I met two sisters at a Carnival parade in Germany. I flirted with the one I assumed was more likely to be single but it turned out she was the one who wasn’t and I had alienated her sister by not flirting with HER, do she wasn’t interested either.

ArrowheadSW · Answer

Hummm... I did have a few fails back in college days... I'd have to think for a minute to recall the specifics... 😅

JSmuve · Answer

Pretty sure "normal girl flirting" isn't directly asking a guy out. Based off of the girls here, asking a guy out is too scary. "So do you like bread" is closer to normal girl flirting.

I don't really have any flirting fails. I have to be in a particular mindset to flirt and when I'm in there, I rarely feel like I failed. I'm also rarely in that mindset.

ZackBan · Answer

Intersting how whenever flirting turns into a serial killer conversion we always end up hooking up. Well 9/10 times at least

MzAsh · Answer

In college I tried to chat up this one guy. Then I found out he was gay.  Now that’s a heartbreak on a whole other level.

fonduegirl · Answer

I was fifteen and looking for a good guy to talk to. I accidentally called him "babe" and he thought that was rather forward so he blocked me

HiveBee · Answer

I think I was like 10 or 11 years old, in summer camp. I said hi to a girl and she screamed bloody murder and ran away from me.

Floppy2112 · Answer

Every time I flirt was the worst failing flirt ever. So the last time I attempted to flirt, was the worst. And the next time I flirt, that will then be the worst.

Wowie101 · Answer

Playing spin the bottle... drubk... went in the closet she puked on me...

babieg · Answer

I called a guy “dude” and thought it was flirting 🤦‍♀️

David_Bayer · Answer

Don't know if it's considered flirting fail but people often say that I flirt with someone when I'm just trying to be nice. It always makes me feel awkward.

The_Maphio · Answer

Tried my hand at a cute girl while camping. Didn't realize her boyfriend was right there.

serious · Answer

I never flirt because I see that as cheap. Hence no such experiences.

douride2 · Answer

Me & flirting just don't go together. I suck at it.

KatherineJ · Answer

I would rather not relive that epic failure. It’s just a good thing that he has a sense of humor...

Massageman · Answer

I never really had the pleasure of flirting, except for some "double entendre" stuff with the ex before my wife.

Jjpayne · Answer

I don't think I've ever tried a flirt but I suppose getting the nerve up to approach then getting shot down by finding out about their boyfriend or kids could count towards that too 😅

Sunnybabe23 · Answer

There is no such thing as a flirting fail.  If the person really likes you, they will excuse your "mistakes". If they are judging you, they are wrong for you anyway, so good riddance!

WowwGirl · Answer

I hit on a bull dike at a bar who looked just like justin bieber on accident.

SpaceGalaxy · Answer

I do not flirt. I just get to the point, like "Pardon me, would you like to have anal sex with me?" or " Can i please borrow your used panties?" and see what she says!

K-I-S-S · Answer

What is this flirting thing that everybody keeps talking about? 🤔

Wiredone · Answer

I don't remember having a failed flirting experience

Pogi-Paddy-2 · Answer

I don't have "flirting fails" only experiences that I wouldn't try again. Everything in life isn't always a fail.🐼

krin_m · Answer

I'm sure in my younger days there were quite a few fails, don't remember specifics. Now a days I don't try! :-) Just enjoy good conversations.

zagor · Answer

It wasn't really flirting but I told a girl I worked with she reminded me of Charles Manson.

KrakenAttackin · Answer

My flirting has always been super low key, so when it failed it wasn't a big deal.

7771999 · Answer

It wasn't really meant to be flirting or cat calling at all. I don't really do either 🤣

Tstrbrainer · Answer

Most of my direct interactions were a failure. One girl even asked me if I was flirting with her.  I was embarrassed. This happened many years ago

Anonymous · Answer

My worst "Flirting Fail" - Hello, how are you? :) -Go fuck yourself loser

Chris_u006 · Answer

I was the person who people flirted with back in the days.
Until one day I ended up gaining people literally talking shit behind my back all day long, those people are no lifers who don't even know me or want to know me.
I even know why it changed, change of political view.

Anonymous · Answer

I suck at flirting. I think every time I text, I automatically end up in the friend zone or the convo dies out

JUST1NC · Answer

Me saying hi and she saying ew :')

karaspara · Answer

😂😂😂 too many to mention

Anonymous · Answer

I was never brave enough to try. I have seen what happens to those who tried but got off the ground awkwardly. Never good.

collie22 · Answer

i try to forget my short falls

COMMODOREII · Answer

I got detention anyway lol

JamieLoves · Answer

I Never Fail! I’m perfect!!🤣🤣🤣🤣🤣

Texasguy99 · Answer

I have plenty I can tell you lol

Bklynbadboy12 · Answer

That's easy with you. You hurt my feelings😂

MrCreep · Answer

Chatting about rope don't help

Hotdmt · Answer

can't remember I say what's up to everybody

MR_Hot · Answer

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What Was Your Worst "Flirting Fail" Experience?

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What Was Your Worst "Flirting Fail" Experience?

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