Share your embarrassing dating stories
- Thread starter Biggalute
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NewOldGuy77
Dude
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Where I live, there’s a monarch butterfly grove. It’s pretty spectacular - thousands of the little bastards in a grove of trees less than a city block. I took a woman there in May, not realizing that they had all left on their annual migration to Mexico. ALL of them. So, basically I took a woman I was trying to impress to see...trees.
munch2much
Intelligence is sexy
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I dated a lady and absolutely fell head over heels in love with her. She pretty soon decided she was a lesbian and from then on only dated women.
I am fairly confident this was not as a result of me as such. And indeed this is the mantra I repeat to myself all these years on, as I cry myself to sleep.
Just to clarify …I made up the second paragraph. That is NOT the reason I cry myself to sleep each night
I am fairly confident this was not as a result of me as such. And indeed this is the mantra I repeat to myself all these years on, as I cry myself to sleep.
Just to clarify …I made up the second paragraph. That is NOT the reason I cry myself to sleep each night
NRJLIVES4ever
Later
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Met a girl for a date and she started the date by stating "Sorry if I seem out of it, I just chugged an entire bottle of Nyquil." It, uh, didn't work out. 
Bry1313
Cock Club 🐓
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Mine was posted in another thread
Post in thread 'Sex & Shenanigans'
https://forum.literotica.com/threads/sex-shenanigans.1589110/post-98322487
Post in thread 'Sex & Shenanigans'
https://forum.literotica.com/threads/sex-shenanigans.1589110/post-98322487
Kittycity
Virgin
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Not a strictly a dating story but still embarrassing..
So had a major crush on a guy from the next door office in my previous job, and both being shy-ish, we were a tad awkward around each other because of (suspected) sexual tension..
One day our paths crossed and we walked up a three story staircase without saying a word to each other, whilst I was desperately trying to play it cool by holding my breath in as much as possible as not to pant in front of him..
After I managed to squeeze out a 'bye' at the entrance of our offices, I walked into mine bursting into a hyperventilating state, dripping in sweat and going bright purple.. my colleagues almost sought medical advice it was that dramatic..
Still cringing about it over a year later
So had a major crush on a guy from the next door office in my previous job, and both being shy-ish, we were a tad awkward around each other because of (suspected) sexual tension..
One day our paths crossed and we walked up a three story staircase without saying a word to each other, whilst I was desperately trying to play it cool by holding my breath in as much as possible as not to pant in front of him..
After I managed to squeeze out a 'bye' at the entrance of our offices, I walked into mine bursting into a hyperventilating state, dripping in sweat and going bright purple.. my colleagues almost sought medical advice it was that dramatic..
Still cringing about it over a year later
ImpishSeraph
My Own Frequency
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- Nov 17, 2007
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I'm my early 20s I had to go to my parents' friend's daughter's wedding. She had a friend that fancied me, so my dad thought it a good idea to set me up with him before asking me. This was in my hippie/punk days. The gentleman took me to a jazz club in Ybor, my old stomping ground. As we were walking up to it, I heard my name yelled and turned to look. I saw a couple friends running up to me thinking I was going to sink or swim, fully punked out.
One gave me a big hug, kiss on the cheek, and twirled me around in the hugging embrace before I could do anything. I went to introduce them to my date, but as I turned to my date, his name slipped my mind. I hadn't met him before this night, not even at the wedding. He had to introduce himself. I was mortified. Both parties were looking each other up and down. Not disrespectful or anything just shock.
It was my first official date. I'm not sure why but I never really went on dates. We always went out as friends in groups. This gentlemen took me on an official dictionary definition of a date.
Needless to say, it was a nice night with dancing, drinks talking etc. He was cute too. He kissed me once when we were dancing and again when he dropped me off. It was the only date like this I have ever had. At the time I didn't even realize people still did that. It felt so 1950ish.
One gave me a big hug, kiss on the cheek, and twirled me around in the hugging embrace before I could do anything. I went to introduce them to my date, but as I turned to my date, his name slipped my mind. I hadn't met him before this night, not even at the wedding. He had to introduce himself. I was mortified. Both parties were looking each other up and down. Not disrespectful or anything just shock.
It was my first official date. I'm not sure why but I never really went on dates. We always went out as friends in groups. This gentlemen took me on an official dictionary definition of a date.
Needless to say, it was a nice night with dancing, drinks talking etc. He was cute too. He kissed me once when we were dancing and again when he dropped me off. It was the only date like this I have ever had. At the time I didn't even realize people still did that. It felt so 1950ish.
ImpishSeraph
My Own Frequency
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So you missed your date?
deft
Jul 🎄
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- Feb 18, 2002
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I had no date. I'm undateable.So you missed your date?
ImpishSeraph
My Own Frequency
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Me too
deft
Jul 🎄
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No! You're impish! That's adorable!
ImpishSeraph
My Own Frequency
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Aww! Thank you 
That was my only date
That was my only date
