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Jason

Dating, It's Complicated: Issue #7

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

In High School, a girl once dumped me by saying “I think I’m gonna date my neighbor instead.”
-Anonymous

I had been dating a girl in college for about two months. One night on our way to dinner she told me that here parents were in town and that they were meeting us there. Being pretty good with parents, I was not too worried. Dinner went ok, and after we went to a movie. After buying a tub of popcorn, her mom opened a rain poncho and spread it over our four laps and dumped the popcorn out on it. We continued to eat trough style during the movie, as I stared down my date and she apologized over and over. I have never felt more like white trash in my life. We broke up a week later.
-Brian, Fl

The first time I had sex with my ex-boyfriend, when I lost my virginity, he asked me afterwards if I felt like a woman. I was going to laugh but saw he had a straight face. I still have no idea whether he was joking or not; I really, really hope he was.
-MJ

I walked in on my parents having sex when I was 5. I didn’t know any better at the time, so they convinced me they were training for American Gladiators
-John B.

On a first date a girl told me: “I can’t wait to get married so I can let myself go.” There was no second date.
-Jon, UF

My last girlfriend said “thank you” whenever we kissed.
-Anonymous K-Vizzle

I dropped my v-card five days before graduating college…
-Matt

My ex-girlfriend gave me a handjob through my jeans. I limped around the next couple of days at school and told people it was due to a knee injury since I was embarrassed to say my penis was rubbed raw.
-Anonymous

My girlfriend in high school was giving me head for the first time. My door didn’t lock so I had to stand against it so nobody could come in, but my little brother and his friend knew something was up so they decided to try to force the door open. I got knocked over my two middle schoolers during my first blowjob.
-Kyle, Radford University

I met this girl when I was in my second year of college and she was senior in high school. She was cute and nice to me and whenever a girl is nice to me I think she’s into me. She was recently single, so I bided my time and waited to make my move. My genius plan was to make my move on Valentines Day. Great idea, right? So I go out and buy flowers and write her a nice card and I drive to her house to execute my flawless plan. Rather than call her to see if she’s home, I just go to her house and expect her to be there waiting. Her Dad answers the door and I ask him if she’s home, she wasn’t. I could have aborted the mission right there but noooo I was determined to finish it. I gave the flowers to her Dad and said “These are for your daughter and tell her I said Happy Valentines Day.” He looked confused and said “Ok…your name’s Tim, right?”. Needless to say my name is not Tim.
-Not Tim

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Plastic Joe

So my uncle steals credit cards. It's kind of his thing. They once called him 'Plastic Joe' on the news, which he wildly objected to, claiming that it made him sound "like a Goddamn vibrator!" Anyway, when I was 11, the cops were raiding our house, looking for evidence to incarcerate my dear, misguided uncle. The whole family is on the porch, and my lazy-eyed dog... Read More » will not stop barking at the asshole police. They tell us that we had better shut the dog up, because he does have the authority to shoot it. I'm thinking that if he even tries to shoot my dumbass mouth breather dog, I'll punch him in the tooth. A couple of minutes later, another officer comes out of the house, and slams down a comically large orange envelope on the table, and blank credit cards and credit card paraphernalia spill out everywhere. The officer has death in his eyes, and demands to know who the envelope belongs to. Nobody says anything. But then smart ass 11 year old me stands up, and says dramatically, "Officer. Those are obviously mine. I'm a mafia crime lord. They call me Plastic Joe." I extend my wrists for cuffs. "Be gentle." The shit hits the fan. The officers get furious, my grandma is trying to tell them I was obviously joking, my sister is calling me stupid, and my uncle is laughing his balls off. 11 year old girl: 1 Cops: 0 Well, I mean...my uncle did end up getting arrested. So...maybe it's a tie.