Single People Admit Their Biggest And Most Embarrassing Flirting Fails

Getting out in the dating game takes a lot of bravery. You either need to be able to show honesty and openess to try and make a true connection. Or maybe that doesn't matter to you, and you're simply looking for a one night connection. Regardless of your intentions, you need to be able to show the person you're interested. For some of us, of course that'd be the time when you trip over a stray dime and spill your scalding soup all over the floor. Reddit user, r/ancientkillerX, wanted to know the biggest mistakes made in hopes of making that connection when they asked:

What's the biggest way you failed when trying to flirt with someone?

Take Me Home Tonight...?

Biggest fail of when someone was trying to flirt with me: I was leaving a party in college, a cute girl offered to drive me home, I said no because I lived 1 block away, she was persistent, so was I...

Took me a couple of days to figure that one out


Keep Your Bottles In Check

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 f---ing soaked her with it.

There is no coming back from that.


You Know They're Two Different Countries, Right?

I was ~18 and trying to flirt with a guy who I was sure had a French accent. I wanted to ask where he was from, and said, "Je suis de France?" which, unbeknownst to me at the time, means "I am from France?" He was completely unamused and goes, "I'm from Hungary."

Ten years later and I've never tried to speak French again.

Or Hungarian.


When Someone Asks You To Take Their Lollipop...

My college crush and I were riding the elevator and she was sucking on her lollipop. She looked at me straight in the eyes and asked me if I wanted it, pointing the lollipop at my lips. I said, "Nah, I'm good." Elevator opened on my floor and I went to class.

I f---ing hated what I did for the rest of the semester.


...Same Goes For A Coke

I did something similar.

So I'm a nurse and there was a coworker I was crushing on pretty hard. He had a bottle of diet Coke or something similar at work one day in which he took one sip out of it, then asked if I wanted to share it with him. However my dumb a-- misheard him, and I thought he said that he picked it up out of a patient's room and that he saw the patient take only one sip out of it so it was "barely used". The thing that I misheard was that he said he took a sip out of it, but I heard a patient did instead. I had no idea he was drinking from this bottle, and I thought he was offering me a random patient's bottle of Coke who went home. I proceeded to belt out "EWW! F-ck no! What's wrong with you?!" while laughing pretty hysterically.

He looked so sad after but I couldn't really understand why until later that night after he went home and I replayed the situation in my head and realized that I completely misheard him.


As Long As You Get There, I Suppose

I'm terrible at missing cues like that. I didn't realize my crush-now-boyfriend had been flirting for weeks until he kissed me. The biggest "no sh-t Sherlock" moment I still kick myself over was that he texted me once and said "I'm sore after working out, can you help me and rub my back?"

He and I lived down the hall from each other, so it wasn't a big deal. I thought, sure, I'll be a good friend. I rubbed his back for a minute until he took off his shirt, telling me it'd be easier. To be fair, it was, but like goddamn I should've known then and there. Instead, I went back to my room and had a crisis over how toned his chest was.


Should've Read More Dr. Seuss

I liked this girl named Sydney and I was like "you know, sydney and pretty rhyme for a reason :)" and she was like "sydney and pretty don't rhyme tho lol".

it was the biggest L of my entire life


Should've just used your finger guns and been like 'That's the point'.

You'd no longer look like an idiot, but you'd look like an -sshole.


Should've Cited Your Sources

Does sending her a five paragraph long email, describing how madly in love you are with her, count?

I dont know if it necessarily counts as flirting, because it wasn't subtle, but it definitely failed lol.


That's Why You Always Leave A Note

In year 1 there was a girl i had a crush on, in my little child mind i thought a good way to get her to like me was to leave those Smiggle erasers, that you put on the end of your pencil, on her desk, smart little child me forgot to actually think about how that would work, she had no idea where they came from and just gave them to the teacher because she thought someone lost them.


When Neither Knows What To Do

Not me, but a guy I sort of had a crush on totally failed at trying to flirt with me.

We had been flirting and bantering back and forth for months and nothing ever came of it. But one day I ran into him when I was shopping at the grocery store he works at. We had not seen each other in like 6 weeks at this point so we hugged and made small talk.

As we were hugging to say goodbye he turned his head and full on licked my face.

It was incredibly strange.


How Do Mouths Work, Again?

Cute bartender I'd been lusting after brought me a drink and sat down with me.

I freaked out so bad I spilled the drink on myself TWICE before I actually managed to get any of it in my mouth.



When The Magic Just Doesn't Hit

I was like 11 on the monorail at Disney. There was a girl I thought was pretty but I couldn't think of any thing to say.

Right before she left for her stop I just said "I like your braces". She looked at me like I had a third eye. My dad had a look of disappointment. It's a moment that still haunts me.


Keep In Mind The Days Of The Week

She was a stranger, we passed each other, and I was maybe hoping to [strike] up a conversation. That was not the right way, that's for sure.

"I love the way you smell."

In my defense, it had been a long week.


Easy Rule: Don't Make Them Think Of Dead Dogs

She was talking about Alaska and jokingly said she thinks her dog could run in the Iditarod. And I responded with, "Hey, just like that one book we had to read in middle school! Stone Fox! Wait, but not the ending."

And we sat in awkward silence for a few moments as I realized I made her visualize the death of her dog that she loved so very much.


And He Was Never Seen Nor Heard From Again

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. Never saw him again.


Avoid Stairs

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 drunken 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 poring from her nose.

I stand up to see her on the floor like this, and stupidly say "your face looks f---ed"

She never spoke to me again


When It All Comes Crumbling Down...

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 "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 her having freckles, genetic impossibilities and deductive reasoning... it was all down hill from there.


Happy Ending, At Least

I was talking to a girl and her friend in a nightclub and it was going well so I figured id whip out the ol 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.


"It All Became A Little Too Much For Me..."

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, on to my crush.

If that weren't enough, upon realizing my mistake I blurted out, I'm so sorry, I love you! 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.


Clever Girl

Fancied a lass for ages i was around 23 her 22 we was heavily into raving/clubbing at the time to 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 and we crossed paths in a club and 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.


Hello, I'm Up Here.

I meant to say "hi" or something but his arms were so beautiful.

I ended up saying "biceps".


Deer Blood...Got You Married? Everything I Know Is Wrong...

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 exhibiting, 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...

This dipsh-t dated me and married me instead of running for his life.

Four years married this May. Love you forever, babe, through brightest day and blackest night.


H/T: Reddit


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