Dating, It's Complicated

Issue #3

by Jason Michaels June 04, 2009

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

I met my boyfriend one day after I had watched a very sad movie in class. He was with some mutual friends when I asked him for a hug to cheer me up. As we were in our first embrace, I heard his friend say, "Hey, we should double team her."
-Sarah

I had been going out with this girl for a couple months, and we loved being passionate with each other. One night we started getting at it kinda rough, we were kissing and I started to use my tongue. All of a sudden she started to suck on my tongue really hard, after about a second I tasted blood. She had ripped that thin layer of skin under my tongue call the frenum. I couldn't talk for a couple of days.
-Anonymous

My high school girlfriend's mother was my mom's gynecologist. My mother "got farther" than I did.
-Anonymous

I have had a crush on a particular individual for a long time. After never getting any signals back, I never pursued it. One day my junior year in high school the girl comes up to me and ask if I wanted to go to a party with her on Saturday. Before realizing what I did, I said "No, I'm going to stay in and watch the new Chris Rock stand up special." Needless to say nothing ever came about after that.
-Keith W.

The first time my high school girlfriend and i ever had sex we were alone in her house taking our time and trying to make it memorable. About halfway through losing our virginity her parents open the front door and her mom shouts, "We brought pizza!"
-Anonymous

My ex-boyfriend and I dated for two years. During every fight he would cry, then ridiculously cry in his room. I found a bunch of used tissues in his room, while one would think they were used for jacking off, they were from crying.
-Dating someone who doesn't cry, NJ

Freshman year I lost my virginity to my then girlfriend. She was on the pill but still wanted me to pull out and I agreed. Being a virgin, however, I was not skilled with the aiming part of pulling out... I then proceeded to facial myself which is embarrassing enough...then it fell off my cheek into her eye.
-Michael W.

So this girl that lived on the floor above me was dating a guy freshman year, who apparently enjoyed eating her chick out (even though she was ugly as hell). One day, however, he ended up in the ER because he thought he had a throat infection; however what he really ended up having was far more disgusting. Apparently the girl had a yeast infection when he was eating her out, and the doctors told him that he had something called "Thrush," which is basically a yeast infection in the throat. The girl actually told people this like she was proud of the fact that she gave him thrush, meanwhile we all just made fun of it behind her back but encouraged her to keep telling people.
-The Man