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Jason

Dating, It's Complicated: Issue #33

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

My girlfriend just said, “It’s scary to think that one day octopuses will become people.” When I asked her how that was going to happen, she answered, in all seriousness, “Evolution.”
-WS

From what I understand, when a guy has sex for the first time, it usually does not last very long. However, it seems I cannot last that long even if it is my hundredth time. So every time I have sex with a girl for the first time, and I don’t last long, I tell her that I have never had sex before. I’m sorry to the roughly seven girls who think they took my virginity.
-Mark, Florida

I tagged along with my girlfriend when her family was taking her to dinner on her birthday. When we were about to leave she was surprised by the staff with a sundae with a cherry on top. She quickly asked “Who wants my cherry?” I stupidly replied yes…. with her father seated across from me…
-Jake, MSU

Almost a year ago I was fooling around with a girl. She got completely naked (with no pushing by me), but before I can get my boxers off, she tells me she doesn’t want to do this, puts on her pajamas, and goes to sleep. I guess technically we slept together.
-Peter, Texas

My girlfriend sleeps on the side closest to the wall so that “the monsters” won’t get her.
-Kevin A., Ryerson University, Canada

So I was dating a girl for 10 months and things were going good and starting to get serious when she abruptly ended the relationship. Her reasoning was that if we ever got married and had kids that I would be lacking in the parenting skills department and wouldn’t work well with children. I am a school teacher and work with kids every day…
-Anonymous

GRIFFINDOR IS UP TO AN AMAZING 30 POINTS!!!
-Carlos, NE

I received a Valentine’s Day card from my ex-boyfriend one year. It was really sweet, until I noticed he had spelled his name wrong. His name is Michael…not Micheal.
-KD, KSU

I was out with my girlfriend and a couple friends and somehow the conversation turned to plastic surgery. The pros and cons etc… To which my girlfriend responded that she had gotten her nose done. She defended it by saying that she hadnīt only gotten it for herself but also for her unborn kids to have “great” noses too. A natural silence followed this where we were all staring at her in disbelief. She was like “What??? What did I say?“ After a pause she was like “OH! Do you guys think that just because I’m a lesbian I can’t have kids“ Needless to say she is no longer my girlfriend.
-Anna

One night after our college football game my girlfriend said she “wanted me” on the floor right then and there. Being a guy, I got excited, took her to the ground and we started going at it. We eventually ended up in my bedroom and after we finished our “fun time” I was laying next to her and she started crying!!! Thinking that I did something wrong I asked her what the problem was. What I heard next completely caught me off guard. She told me that she felt horrible because she thought her grandfather that had died over a year ago was, “watching her from above.” Please let me know if there is a correct way to respond to that because I certainly didn’t know what to say, maybe that’s why I am single now.
-Anonymous

I’ve been deciding whether or not to share this, so here it goes: I was at a soccer tournament, and along the way I meet this girl who seems nice. She tells me to meet her at her room, and then we can get some coffee. 20 minutes later, I knock and she answers the door in her towel. Being 16, I shyly ask if she needs more time, but she tells me to come in. After parading around naked, asking me if she should wear underwear, she sits down next to me and says “we should f**k”. I say I’d rather hook up, and she goes “no, i don’t do that. Just sex.” So I try to ask if she has protection, and she answers “I mean… I’ve got a ziploc bag.” I just walked away.
-Anonymous, France

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Virgin

When I started dating my boyfriend, he was a virgin in every sense of the word. He had never even held hands with a girl. When we were making out for the first time, I licked his lower lip. His whole body trembled and he muttered "Oh dear god." It was so funny that I had to stop completely because I was laughing so hard. We're on month eight now.