Dating, It's Complicated Dating, It's Complicated
 

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Jason

Dating, It's Complicated: Issue #5

Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me at dating.itscomplicated[at]gmail.com!

My sophomore year of high school I was dating my boyfriend for a few months. One day I told him I had something to show him in my room upstairs. This was the first time my boyfriend was allowed into my room; we were alone together. He goes straight to my compter and tells me I need more RAM.
-No Longer Dating A Nerd, CT

My girlfriend dumped me for a guy named Chaz.
-Anonymous

I had a huge crush this girl when I was in 7th grade.  I invited her, along with the rest of my class, to my Bar Mitzvah.  After much persuading from my friends and her friends, I finally asked her to dance.  She said no.
~Ev

On my very first date, I took a girl to go see “Knocked Up”. Needless to say, it was very awkward when I was spent the rest of the night trying to get into her pants.
-Dave, University of California, Irvine.

I got so high and drunk one night that I shit my pants and didn’t realize until the next morning when he was pulling my pants and underwear off to go down on me.
-Anonymous

I started seeing a girl in College and one night she came over and we fooled around for the first time. She unzipped me and gave me a handjob while we made out. I came pretty quickly. I was embarassed, but she didn’t seem to notice. We kept making out and she kept stroking cause I was still hard.  After a while I got bored. I decided to try to fake the orgasm, then she would see the huge stain between us and not know I came so early. I went for the fake, but she didn’t seem to notice that either. Still making out, I tried again. Nothing. At this point she had been going for a really long time and I was getting frustrated. I decided to give it my all, and really sell it. She just kept going. Finally I just took her hand away and told her “I’m done.” She saw the stain and seemed confused. She didn’t notice any of my 5 orgasms (only one being real).
-Chris

So just the other night, my girlfriend had gone to a friend’s party and was supposed to go back to her house around 11. I get a call from her sister around 11:15 asking if she was with me. Apparently she had left the party early and no one knew where she was. She didn’t answer anyone’s call including mine. I then got a tip from a friend about where she might be. I go by this guy’s house and sure enough, her car is outside. As I wait for her to come out to her car I decide to take one of her wheels off. I get done with that and get a call from her. She said she had gone with a friend to the hookah bar and forgot her phone in her car, but she was on the way back home. I ask her if it’s hard to drive with a missing wheel. She opens the front door to see me standing next to her car. I get in my car and leave.
-Luke S. UNCG

After getting out of a semi serious relationship, I had gone out on the town with a few friends to have some fun and meet some new girls. I wore my lucky hat, I got from my grandpa who died not too long ago, just in case. About halfway through the concert, a pretty hot girl walks up to me and my friend and says “I really like your hat!” But without thinking at all, the first thing I said was, “Thanks! It was my grandpa’s. He’s dead.” After that, she immediately walked away and I went home alone that night.
-Anonymous
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Footsie

My boyfriend and I had started sleeping together, but hadn't been doing so for too long. We were still getting to know how kinky the other one was. So one night after hanging out he went to go get ready for bed I went and laid down in his bed naked, pretending to be asleep. I heard the door creak open, heard him walk quietly up to the foot of them bed, and begin slowly and... Read More » sensually licking my foot. I froze, completely repulsed and unsure how to react. I turned around to face him, and explain that I just wasn't ever going to be into that sort of thing, and could this even work out? . . .only to find his roommate's pitbull wagging her tail and licking away and my oblivious boyfriend still in the bathroom.