Dating, It's Complicated: Issue #20

One time my friend and I were talking, and he decides to just blurt out to the girl sitting across from us in class that I liked her. I had no time to reply to this before the girl looked me in the eyes, with a completely straight face, and said “Ew” and continued working on her assignment.
-Anonymous

During 6th grade year I asked some girl if we could go out during the last period of school, she said yes. After the period ended and I was on my way to my school bus her friend came up to me and told me that she had broken up with me. I cried the entire bus ride home.
-Ewout, Kegweed Community College

I was dating this girl from Long Island and she was telling me how it should be separate from upstate New York. She went on to say, “Yeah, Long Island should be the 52nd state.” I looked at her with a face of disappointment and asked her, “Wait, what is the 51st state?” She looked at me confused and said, “Please tell me you are kidding, you can’t be that dumb.”
-Steve

I had to have jaw surgery when I was 21, so I had braces at 22. When I asked a girl in my short story class out, she asked me how old I was.
-Matt

My ex-girlfriend came up to one day and told me she just learned that there is a difference between Washington the state and Washington DC.
-Jake, Purdue

I had been dating my girlfriend for 2 years at the time. I was leaving for a camping trip in Minnesota and would be gone for her birthday. I bought her flowers, a card, chocolate and a necklace. I paid a friend of mine to go to her house in the morning and hand her the goods. She responded with, “I’m breaking up with him when he gets back, you can keep the flowers and chocolate.” She kept the card and necklace. He decided to give me my money back.
-Zack Hall

I told my girlfriend that my mom wanted to take us to see a famous musician like Stevie Wonder when he comes to town. She responded by saying “Oh really, I love magic!.” I’ve ever laugh so hard in my life.
-Steve Northeastern University

After my (ex) girlfriend and I lost our virginities together, she started saying how she imagined it would’ve been with her ex-bf. I hadn’t even taken off the condom yet.
-Jerry

The first time I meet my girlfriend’s parents, we ended up in a real awkward silence at the dinner table. It was then when my friend called me. My ringtone was “fuck the police” with NWA. My girlfriend’s dad is cop.
-Anonymous

I dated a girl my freshman year of college and, when making out with her for the first time, noticed that it was a particularly sloppy affair. When she said “This making out is a very messy business, isn’t it?” it dawned on me: She had never made out before. She confirmed this fact. We didn’t date long.
-Johnny

My girlfriend turned to me once confused after watching the zombie movie “28 Weeks Later” confused how the zombies never left England. She asked me if England was an island or was it connected by land. I laughed and she got mad. “Well I thought that was what the English Channel was, that’s how people drive between England and France!” She’s 28.

-Anonymous