Dating, It's Complicated

Issue #5

by Jason Michaels June 18, 2009


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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