What is one of your most embarrassing moments while flirting/dating?

[GeminiDiamond]

It's not my most embarrassing but top 5. I was walking while checking out this person, and they looked over and we made eye contact, I smiled, and they smiled - slow motion started, and we held that golden trance for a few moments just before I walked right into a street lamp. It made this awful sound and hurt like hell. I was so embarrassed that I didn't even bother to look back, bright red and walking fast as I could away. What is something that happened to you while flirting with/or dating someone that was embarrassing?

Updates

+1 y

First, I wanted to leave out -while flirting/dating but I couldn't pick Other for an option. Also, the best laugh is when you can laugh at yourself. Happen so long ago. I laugh about it now.

[236color]

I got very sick at dinner on a date with my high school crush. We ordered dinner and before it got there, I felt so bad I handed her my wallet and went out to lay down in the back seat. When she came out, I opened the door and threw up in the parking lot. She had to drive me home. Decades later I met her and she told me 2 things to make it even worse. First, "I would have gone out with you again, but you never asked me." Second, she caught whatever plague it was I had a few days later.

[PeterLegg91]

While me and my then girlfriend were walking she was wearing flip flips and she spun and fell over 😆 she hurt her ankle and it bruised up and had see an expert for it 😆 I felt laughing she got angry ITS NOT FUNNY PETER (angry)

[Billlewis]

@PeterLegg91 I just started following you and I'd like to invite you to follow me as well, if you want. Thank you very much.

[D_Bone_Steak]

I've told this story before, but I'll drop it here again.

I met a new girl in Japan, talked her into hitting the movies with me the next night. She basically expects me to pick the movie. I couldn't read Japanese yet at that point, so I was just looking at pictures. I thought I was about to see a survival, guns blazing Western movie.

It was fucking Broke Back Mountain. I was in Japan and nobody told me my fellow Americans started making gay ass movies.

It still gives me the cringe and whatever the ick is to this day. I'm pretty sure that girl was thinking I'm a bussey man butt lover or something. Long story short... that's one of the very few times I didn't get any pussy after a date. Gee... I wonder why? Those movies should have a warning label..."WARNING: This is Gay"

[GeminiDiamond]

Lol, kinda your fault, too. She was probably like, "Let's go to Broke Back Mountain" in Japanese. You: Sure. Total Backfire. Good one

[GeminiDiamond]

Oh, miss read that! Haha, you picked it.

[DishLady]

I was out with a guy from a very different religious group. It wasn't till we were at the coffee shop that I realized... I was there to interview him and he was there flirting with me... Thankfully I was very familiar with the place, the owner, etc., so the waitress knew who I was and asked for my order... and I asked for a Greek Orthodox coffee instead of a Greek coffee. Her lips twitched as she wrote it down, asking if I wanted a single or a double...

In my defense, I hadn't had any coffee yet and it was around 7am... the guy had a flight to catch and I needed to interview him for an article I was writing.

To this day (~10 years later), when I pass or walk into that coffee shop the owner crosses himself and asks if I would like a side of incense with my Greek Orthodox coffee. (SIGH...)

[curiousmandy]

Aww! That is so cute and admittedly funny! Thank you for sharing that.


My most embarrassing by far was flirting with an older guy in a grocery store one time and then his son came back over to him and was a guy I went to high school with. OMG that was so embarrassing

[GeminiDiamond]

Zomg, awkward. What did you after he came up?

[curiousmandy]

I got all awkward, his son and I talked for a few minutes and his dad and I talked a little more. I told him how nice it was to meet him and embarrassingly walked away lol

[GeminiDiamond]

I wonder what they talked about after? Hopefully, when talking to the dad, you found out when he'll be shopping next 🥰

[curiousmandy]

I wondered about that too! I’ve thought about trying to look him up online to see if I can contact him but then realize how cringy that would be

[Anonymous]

It was like 6am, I went for a donut run, got my donuts and was heading back to my car along the sidewalk. Caught the eye of this gorgeous man in a suit, so I'm trying to catch his eye, and I do, I smile and then whilst occupied, I didn't notice this piece of wood jutting out of the sidewalk which I proceeded to trip over and go sailing head first into a concrete pillar. The wood reverberated back to the concrete making the loudest sound possible, which caused everyone else around to turn and look at me. Barely managed to save myself from hitting the pillar, I look up, the guy is giving me a weird look, I start laughing because I do that when completely mortified, and well, let's just say as I slinked back to my car, with my donuts as my sole consolation prize.

[19magic]

It's not too bad, but in the library where I used to study we had the long harry potter style tables and I said to a mate of mine damn that guy in the blue shirt is cute and said guy looked right at me and smiled, to which I then go eek he's looking and blushing like mad.

[NathanDavis]

she was already my girlfriend, but our "second kiss" I did hit the door with my head while I was leaning to kiss her... lmao

I really didn't feel embarrassed... but it was hilarious

[GeminiDiamond]

Seriously, going to knock you out

[NathanDavis]

but, the door started it...

[GeminiDiamond]

Lol ugh... still going to going to knock you out, silly Davis

[NathanDavis]

I'll pretend you did... but then, what would you with 200lbs of knock knocked out jokes...

[GeminiDiamond]

No, I'm going to knock you out

[GeminiDiamond]

You're going to be zzzzz, don't care how big you are

[NathanDavis]

can you even reach... lol

how tall are you again?

[GeminiDiamond]

Tall enough, I'll hit you I'm your nuts

[Lynx122]

Most of the moments were just me being either too passive or not aware that the girl likes me but it's ok. I had a lot on my plate growing up and I think it would've been too much for me. Now I'm in a relationship and I have a lot to catch up on, but I could use the time before, to learn more important life skills, so I think it was worth it :)

[DryGermanGuy]

I fell asleep while she was talking with (to) me. To my defense, I was dead tired from work, laying comfortably and she had a very soothing voice. :-)

[Anonymous]

He was ‘shoving’ me a cookie to which i thought he wants to feed me, i confidently just take a bite of what he fed without holding it just to make him surprise because of that🤣 I later on had to pretend i dont want to dirt my hand hence i do so

[Gialboy]

Flirting in my garden without notice that the neighbor was there listening to everything..

[GeminiDiamond]

Master-flirter, gotcha.

[exitseven]

I told a girl I was falling in love with her. She told me I was crazy.

[Kelly6]

@geminidiamond What you had was embarrassing, no questions asked.

[killake-ko]

I had to find a bush to go pee in while on a date. Don’t worry she saw nothing. We continued our date as if nothing happened.

[serious]

I never flirt and I have never dated in my life so there were no embarrassing moments.

[strateguy632]

i said the wrong name oops!

[GeminiDiamond]

I've done that as well. 🙃

[Anonymous]

Once I didn't get erection while we were gonna sex.. because I just masturbated a moment ago.. lol

[GeminiDiamond]

just give me about 5-10 minutes! Don't go! Heheh

[Opinion Owner]

What you mean?

[GeminiDiamond]

I mean, don't guys take about 5-10 minutes to stand back up again? Or?

[Opinion Owner]

Yes.. but I was feeling ashamed before 10/15 minutes lol

[Opinion Owner]

After it sex was more great by the way 👍

[ChicoFromThe305]

Some things are just meant to die with me

[MasterKS]

what embarrassing about it? its an accident.

[chenyu]

I won't be embarrassed

[caringguy56]

Once something happened lol

[Brad08]

Forced to talk on phone while being pegged

[impalabill77]

I can't remember any