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* Gin
VIP April 2013

Let's have a laugh-Share your most awkward/worst dating experience!

* Gin, on June 25, 2012 at 1:51 AM Posted in Planning 0 41

This should be fun!

Share your most awkward/worst dating experience!


41 Comments

Latest activity by Linda E: Fairy Godmother, on June 26, 2012 at 10:16 PM
  • * Gin
    VIP April 2013
    * Gin ·
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    A friend of mine convinced me to go out with a friend of hers, she though we'd have a lot in common and hit it off. She lived an hour from me and I was visiting her for the weekend, so I agreed to go out with her friend one night while I was there. We had dinner, good conversation. He was a really nice guy. We were at downtown Disney in Orlando and after dinner we walked around the boardwalk for a bit. We had previously chatted on the phone and I had mentioned that I liked John Mayer. As we got to a spot on the boardwalk, he stopped, pulled out his phone and proceeded to play John Mayer's "Your Body Is a Wonderland" and asked me to dance, right there in front of anyone walking by. All I kept thinking was "You have no idea what my body is and now you definitely never will". It was just too awkward for the first date IMO.

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  • Iris
    Master February 2014
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    Awkward conversation with FH: We met thru a mutual friend, via myspace back when it was cool (then got replaced by FB lol) Anyway, he sent me email & introduced himself, little did I know he was trying to get to know me for dating. I thought oh our mutual friend, was just being nice - back then I had a crush on said mutual friend. So we were talking in message, but somehow I let it slip that I was crushing on that friend. FH was like, oh um, sorry but he thought you would be into me, that's why he told me about you. Oh shit! I felt so freaking embarrased, I apologized but the damage was done. Real awkward, & even on our 1st date FH was like, so still crushing on him? I gave that nervous laugh & felt so bad for it.

    lmao needless to say I long lost that crush & well 2 1/2 yrs FH & I are still together. Said friend is a good hangout buddy, & I barely knew him back then. Now I know his personality, soooo not my type!

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  • Cyndi K
    Master August 2012
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    I had a blind date when I was 15. Since were younger (he was 17 and from a different school) we just went to a local drive in and got ice cream and went to a park for a baseball game. I was much much MUCH smaller then and this guy was buff I guess he was trying to show off his strength cause before I knew it he was lifting me up then let go of my upper body so that I was hanging off one of his arms by my knees! It happened so fast it freaked me out a bit and then he went to swing my upper half back up to "catch" me but he was standing too close to a picnic table and cracked my head on the seat. It hurt like hell and to make it worse he said "oh my God" and dropped the rest of me. I ended up with a huge goose egg on my forehead with a matching bruise. He felt really bad and kept saying sorry so we went onto the baseball game but that was it. He was cute and all but I was afraid what he'd do next time he wanted to show off lol.

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  • Iris
    Master February 2014
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    Worst experience: oh but there are so many lol... I'm 27 but flash back to me being 22, just getting divorced(not legal yet) new to San Diego (Army, was stationed in RI) & trying to get on my dating game - didnt realize it back then but I was on major rebound mode. So I meet a guy online, sounds legite, sounds awesome. Lives 2 hrs away. We agree to meet in the middle, & he takes me out to this bar where we play pool & get really drunk. I'm not the type to have one night stands, I like to be in a relationship. But this was one of those nights, we did it in a park, on a freaking bench! Top it off with, we didnt use protection. I was drunk, but I remembered it all, esp after seeing bruised on my back/butt from the bench. We ended up driving back to his town (thank god no DUI) slept in his apt, & I did the morning walk of shame, to his truck lol. He had to drive back to where my car was parked. We sat in silence the whole ride - except for music

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  • Sara
    Super July 2012
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    IDK if it would classify as a date but there was a guy I had been talking to and he was very persistent. I had talked to him one night and said I was staying home. Well a girlfriend called and we went out. Low and behold he walked in with a date... He even forgot her name when he introduced us to her!!! You could see the panic on his face. It was pretty funny!

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  • krisalicious
    Master April 2012
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    OMG those are painful. Cyndi - literally!

    So I once showed up 20 minutes late for a first date without calling. It was dumb scheduling on my part and a really long story but anyway, by the time I got there the poor guy was super annoyed and almost done with his coffee. IDK if he stuck around out of morbid curiosity or to try and be a gentleman or what, I would have been out the door after 15 minutes.

    Anyway, I was so flustered and felt so bad, I started stammering about all kinds of dumb crap. I had just gotten this stupid forward email about pirate jokes and I blurted out for no reason, "Hey, did you hear it's international talk like a pirate day?" and then I said, "Arrrrrgh you gonna get another latte? Haha!...no? Oh, um, okay." Awwwwwkwaaaaaard. lmao.

    Yeah, that guy never called me again. Whoopsies! Smiley smile

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  • Allison
    Expert August 2012
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    I went out with a guy I met online, and on our first (and only) date, he told me that he was a professional pool boy. Naive me asked, "Oh, so you clean pools?" Nope. He laid around rich, lonely, old ladies' pools and did things to them for substantial tips. Wow! Needless to say, he didn't get a kiss goodnight.

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  • M.S.P.D
    Master August 2012
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    A friend of mine and my sister's called me to ask if I wanted to go to see a movie. I said okay but I had to be back early because I was hanging out with someone else later on. Then he drove me over 2 hours to the coast where we watched a movie. I was a bit confused but went along with it. Little did I know that he thought it was a date. Apparently we had been on several dates that I didn't know about. Yeah.. that was an awkward conversation.

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  • Katy
    Expert May 2013
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    My freshman year of college I had just got out of a serious relationship and wasnt looking to date at all, but my bestfriend was talking to a guy and he wanted to go on a double date because he didnt want to go alone. So obviously i was hooked up with theis guys friend. We went to a movie and then a party after, the movie was normal and then when we got to the party the guy I was supposed to be on a date with tried to make out with me and then the guy my friend was on the date with asked me to have sex with him! I told my friend never again!

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  • krisalicious
    Master April 2012
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    OMG Amy, I have heard THE worst dating horror stories from my girlfriends who were single in L.A. I think you all should win a prize. Smiley smile

    This isn't my story (I promise!) but it's pretty funny - one of my friends went through this crazy girl phase after a bad breakup where she was doing lots of tequila shots and meeting guys when she was drunk in bars. One guy came to pick her up from a date and she was all nervous b/c she couldn't remember what he looked like. When he got out of the car she blurted out, "Oh right, you're the Asian guy!" lmao.

    I think that was a pretty brief evening. Smiley smile

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  • Amanda
    Master July 2012
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    Wow, some of these are so horrendous but funny!

    I have had a few horrible dating experiences, but this one was the worst. I was 21 and just out of a very serious relationship with my high school sweetheart. I agreed to meet this guy for lunch who was a mailman. We went to a nasty Chinese restaurant where I had to explain that I was a vegetarian because he couldn't understand why I wouldn't eat meat. After I told him I don't eat meat, he said "Oh, does that mean you don't suck d***?". Seriously. I didn't even know what to say. We left shortly after that and I got a text from him saying "So what do you think?" I said "About what?" He said "About sleeping with me?" I said "Are you kidding me?" He said "No, I have been with 35 women. Women want me." I just told him I wasn't one of them and to never text/call me again.

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  • Dex
    Master September 2012
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    Mine is short and sweet. I tried match.com for a bit and met a guy, he seemed real nice so I decided to meet him for dinner. Five minutes into dinner he asks me if I liked to be choked in bed. I kindly excused myself from the table and never looked back. Lol

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  • Marie S. (aka Princess Leia)
    Master October 2012
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    My two worst dates both came from JDate.com - the first dude - turned out to be unemployed & asked me for a job (I owned a small biz at the time) from there it just went down hill - we went to the mall where he proceeded to tell me about his love for Ferragamo shoes and he had to try on 3 or 4 pairs. While in the shoes, he starts doing the Hustle and tells me that he belongs to Hustle Dance Club and he can't wait for me to go with him. All I could see in my head was John Travolta in Saturday Night Fever - no way... Never called him back. Yuck!

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  • tiedaknot™
    Master March 2013
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    Mine was the first time I went to FH house for dinner. We ate dinner and went out back to sit on the deck and listen to music. We were looking through sales fliers and listening to the music when I suddenly smelled something awful! I looked up and said "Good lord man did you sh*t yourself?" poor guy...he let one slip that was silent and thought it would be ok since we were outside...He was so emabarrassed =) That was pretty awkward but we got through it and it is now one of our funniest memories

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  • Marie S. (aka Princess Leia)
    Master October 2012
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    Second dude - was a younger guy. I was 35, he was 24. So we met for a drink at the Four Seasons in Philly at midnight - I thought it weird but was willing to go along with it. So we're sitting in the lounge having a drink when he suddenly jumps out of his lounge chair and pounces on me w/ this giant wet sloppy kiss and full body contact. I push him off and tell him not cool, slow your engines down hon. A tad later we go out for a smoke - I'm leaning against the wall but he's in my space making me uncomfortable - don'tcha know he moves in, again full body contact and is trying to dry hump me against the building and bit my neck like a vampire. Pushed him off and said I gotta go. I actually had a hickey from that bite. Needless to say I didn't call him back either.

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  • Tyra
    Expert December 2012
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    I went on a couple of date with the cutest guy. Super tall, super ripped. Sadly he was also super dumb.

    So, dumb that I wanted my friends to witness this because I couldn't imagine someone being so clueless and needed witnesses. I took him to dinner at my friend's house. My friends tried to include him in the conversation (my friends aren't einstein or anything, it was just typical small talk) but he was mostly confused. My friend made twice baked potatoes and he actually asked "was it hard to bake something twice, weren't you afraid it would burn?".

    After this EPIC FAIL dinner on our way home, he looks at me and said "'I don't think this will work. You friends are too smart and you read. I think I want to be with a girl who doesn't read."

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  • Kristen
    Master September 2012
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    Haha oh wow these are hilarious!

    My weirdest date was with this guy I had met at a bar the night before. He seemed cool, not like most guys I had met at bars, so I agreed to meet him for coffee the next day. We had a normal, boring chat, until we got to talking about our pets. He was traveling on business, and he told me that he loved his dogs so much that he lets them sleep on his pillows and then brings the pillows with him when he travels so he can have their fur and smell with him. Then he proceeded to show me about a hundred photos of his dogs on his camera. I love my dog, but there is no way in hell I'd let him sleep on my pillow and then bring it with me on a trip! Gross. Never called that guy back, needless to say!

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  • Stephanie
    Dedicated August 2014
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    I went on a blind date with a friend of my friend's boyfriend. I was told as we were pulling into the parking lot that the guy's nickname was Toad. I didn't want to leave the car after I found that out. I finally got out of the car and walked into the lobby and saw him. Yeah, the nickname Toad fit him very well. To make it short, I was so not feeling any part of this date, I was soo extremely bored that I ended up falling asleep 20 minutes into the movie. I was so p*ssed at my friend for setting me up with this guy that we didn't talk at all on the ride home.

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  • Sara
    Super September 2012
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    I can't think of just 1 or even 2 most embarrassing or awkward moments- I feel like virtually my entire dating life was awkward and embarrassing! I was a late bloomer and really shy untill I found beer at about 17. haha. But I def made up for lost time in the 7 years or so between then and meeting my FH. Most awkward moment w/my FH though- the 1st night we offically met we got SO drunk w/our mutual friend and hooked up. Super awkward the next morning, and I asked for his #, not the other way around. He was too embarrassed to ask me. Then our mutual friend had to field calls between us to her b/c we were both so shy and awkward about the whole situation. We ended up going out a few times and decided to wait to get physical untill we knew each other a little better- we already knew THAT chemestry was there. lol. Come to find out we hit it off and have spent virtually every day together since, we waited a whole whopping 2 weeks after our initial "try-out" as we joke

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  • Ryan
    VIP July 2010
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    This wasn't a date, but when I was in high school I was at the mall and some guy was browsing the shoes near me (up and down two aisles) before turning to me and asking, "Do you think when we know each other better, we can f***?" I said, no, I dont think so, and he said "You don't know me, I'm pretty cool" before I decided that I could buy new shoes somewhere else.

    Oh, there was the guy in college who took me to Chuck E Cheese for my 19th birthday (awesome!) but worked the 4 am shift at a restaurant, and was annoyed when I called and woke him up at like 8 pm, and another time in the middle of the afternoon...I don't like people who aren't nice when they answer the phone Smiley smile

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