Embarrassing Dating Stories: First Encounters

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When we were younger ours “firsts” used to be so exciting, with no fear in sight. First birthdays, first haircuts…then our teenage, and eventually college, years hit and the idea of first dates, first kisses and first times where overshadowed by the looming feelings of nervousness. College Magazine readers share their most embarrassing, hilarious, or just plain disastrous stories from their first encounters with a date or hook-up.

“On my way leaving a class last semester I saw this smoking hot girl, I mean amazing, a girl way out of my league, just sitting by herself. Now normally I would just keep walking but that day I told myself, ‘Andrew you can do it, go make it happen.’ So I walked up to her introduced myself and just started talking and she was digging it. We sat there and talked for at least 30 minutes and the girl just kept getting better and better. In my state of euphoria I just blurted out, ‘how about we hang out Friday night, watch a movie or something?’ I couldn’t believe I said it! Then she replied, ‘Sure! My boyfriend and I will be there. I’ll bring the movie.’ I’m sure she saw my pride crumble right in front of her.” -–Andrew Billups, Buffalo State University

“For my first date after a disastrous break-up, I let my best friends pick out my wardrobe, which turned out to be the worst mistake of my life. They dressed me in a skintight dress and five inch heels. I looked great, but walking in heels wasn’t my specialty. My date met me at my apartment and as soon as we stepped onto the gravel, I fell face first. Not how I imagined starting the date.” –Paris London, Westchester Community College

“My freshman year, I went to my school’s Greek houses to celebrate Halloween and after [some] jungle [juice] I was completely wrecked. I ended up hooking up with a guy outside and had to physically push him away so that I could throw up all over the lawn, accidentally getting some on his shoes. My friends had to carry me to the car and because my costume was extremely short, it allowed everyone to see my bright red panties! –Skyy Brown*, Pace University

“I only have really one guy that I could consider my brother. We met in high school and stayed friends all throughout college. During our senior year, he decided to ask his long-time girlfriend to marry him and I was excited for him. Then he asked me the unthinkable: to help him shave his behind. I was not going to do it at first, but that's my best friend, so I decided to help. Mid-shave, my girlfriend barges into the room without knocking and catches me, face-to-butt. I was so embarrassed. They laughed about it for weeks.” –Vikktor Perez*, Westchester County Community College

“After I came out to my parents, I decided to bring my first official girlfriend over to the house. When we walk inside, my dad was sitting at the piano belting Ray Charles. When he saw us come in he began to get louder and even proceeded to introduce himself as Ray Charles. He thought it was funny and my girlfriend thought it eased the tension. I just felt like my parents were the most embarrassing ever.” –Sherry Day*, Holy Cross

Junior > Magazine Journalism > Syracuse University

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