What was your most awkward dating experience ever?
October 11th, 2009 Posted by: admin
The worst I ever had was actually a double date, a very good friend of mine had asked me to go on a double date with him and a friend. I was head over heels for this guy and said yes. He then told me that his friend was ***. I had no problem and stated I would bring a friend as well. So, the night we were supposed to go to a club, I went to the guy I had the hots for’s house. With my friend Jason who was *** as well, thinking to hook him up with hottie’s friend. (Blind dates are ALWAYS BAD IDEAS). Hottie opens the door, and standing there is him and the second most attractive man I’d ever seen in my life! I was so excited for Jason (My best friend) that I had gotten to hook him up with this dreamy man. That is, until the intro’s were made (hottie leaned over and kissed #2 hottie) as his boyfriend. Well, that was a load of fun… *sarcasm* So anyway, that night I was designated driver for 3 drunk gorgeous men, and trying desperately not to turn red every second. Lesson: ALWAYS CLARIFY!
By: *jen*
By: *jen*
Tags: Attractive Man, Best Friend, Good Friend
October 13th, 2009 at 11:50
Okay…………….?
October 16th, 2009 at 20:18
ummm, I want a movie of that.
My most awkward experience? I met this guy at a party who I felt was 1) hot, but 2) sketch. After a lot of pleading, I did give him my phone number as I was new to the area (Washington DC). He ended up calling me and asking me for dinner, and I said fine. But that was like 2 weeks into the future because he was leaving the country. He ended up calling me when he got back into town and wanted to know if I wanted to get a drink. Always up for that, I said fine. Met him at his house and, because he just got back into town, he was busy catching up on mail, phone messages, etc. Then he disappeared into the back and asked if I was ready. I said yes assuming he meant grabbing a drink. What he REALLY meant was grabbiing my clothes and tearing them off because there he was, standing ***** at FULL attention. I was like, c’mon, at least buy me a drink first (lol)…anyway, I was a bit shocked and got outta there pretty dam fast. Totally creepy.
Then he had the nerve to have is SECRETARY call me and cancel dinner. I just laughed. NBD at all. Like I said, total sketch.
October 18th, 2009 at 14:55
Awkward for you…..hysterical to read, print out and share around the office!!!!
My most awkward dating experience? At 22 I was out with friends and this really well built blond guy started talking to me - eventually he asked for my number, blah blah blah we set up a date for later that week. Date day comes we have a nice dinner, good conversation - end up back ay my home for drinks and maybe some kissing. We settle on the couch and are getting comfortable and he says, “Mind if I take off my foot?” Then proceeds to remove his prosthetic foot, he lost it as a young man.
Now remember I was only 22 and not that experienced in life - so that freaked me out and things got awkward and went downhill from there. That was our one and only date.
I am more mature today and something like that would not be a big issue for me at all!
October 19th, 2009 at 01:35
Honey, it is entirely TOOOOOOOO personal to discuss in public!
Take my word for it.
October 20th, 2009 at 02:45
I don’t know if the worst dating experience counts as the most awkward, but when this happened to me, I was very new to the dating game. Here it is, the experience, which i already told someone else on this forum
(my story is right beneath the question)
I must say I was naive then, and the lesson learnt that time was no cyber dates till you know for sure what you are getting iinto. I still mess up sometimes, like when I went out on a date who turned out to be my ex’s ex!!!!
October 21st, 2009 at 18:46
oh Jen! LMAO. Poor baby…I think you win. I went on a date with a guy once (pre-lez) where all he talked about was his John Deere. Bad enough…..
October 22nd, 2009 at 01:19
I went on a date with a MTF transsexual, and apparently she had a foot ******. She wanted me to take off my shoes and rub my feet with hers. She also wore ballet slippers to our date, so that she could take her shoes off easily and rub them on my feet.
Now, I don’t have a problem with people’s diversity and personal expression, I just didn’t feel that showing my bare feet in a public restaurant (even if it WAS under the table) was appropriate or hygenic.
October 24th, 2009 at 04:07
Ok this is a totally true story and why I wont date from the web ever again.
I meet this guy on line every thing was great he seemed real sweet, we talked on the phone decide to go out.
My first mistake. He picks me up. We are heading to a local bar on Tuesday night. Have a few drinks in an otherwise empty place, this guy is cool smooth says all the right things. So we are heading out of there and I don’t know if its the hooch, the full moon, or the fact that I haven’t been out in a llllooonng time at this point in life; but I am really close to inviting this guy in to my place when we get back. Then the dark night fills with red and blue lights. I mean FILLS like from what seemed to be about 50 police cars in all directions a helicopter has a spotlight on us from above and there are guns pointing at us even before we stop! Again this is a true no BS story.
As we stop a menacing voice sends chills up mine spine as he shouts directions to the driver (we will call him **** from here on out.) over a thunderous pa system. A polyester pig pile instantly covers **** as soon as he opens the door. The same fait awaits your humble narrator. After being in the back of a squad car and having the FBI questioning me for about 10 min the knew I had nothing to do with ****.
It turns out that **** was quite a bad person who had been wanted by the feds for a long time. They wouldn’t tell me much more than that and since the cute one gave me a ride home I was just happy to not have handcuffs on anymore.
That’s why I don’t date guys from web sites.
October 26th, 2009 at 21:25
I was just barely cracking the closet door open when I talked to a guy from a personals ad and we agreed to meet for dinner. This was my very first date with another guy.
We go into the restaurant and sit down at a table. Five minutes later some people I knew from work come in and are seated at a table next to us. Since I was not out at all, it led to a very nervous evening with me wanting to leave ASAP. After leaving the restaurant I told the guy that it wasn’t him, and that I didn’t want people I worked with to know, but that was both our first and last date.
October 27th, 2009 at 12:26
Mine was horrible, awkward and embarrassing. I live in Atlanta. I was dating a guy in Florida. I went to spend the weekend with him. We went out for drinks. We went to a bar where a ex of mine worked. The guy I was dating was very cool with it. Well my ex was the bartender. He gave me a shot of Tequila. I had just eating Sushi. I threw up all over myself at the bar after I took the shot. It was horrifying. Needless to say no more Tequila for me ever again. It was awful, just awful.
December 29th, 2009 at 22:17
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