How I Fumbled The Bag - Part II: Serena

She gave me another chance and my younger self blew it

I was cripplingly insecure in high school. I gained some confidence after losing my virginity to my first girlfriend at 15, then lost it after we broke up at 18. It was my first real heartbreak. For 2 years, my confidence level was below zero. I was an angry kid who hated women. This, of course, deeply repelled them.

I took a Biology lab with one of my friends freshman year. One day we got paired up with two girls. The first girl’s name was Danielle. My friend ended up dating her for a few years. She looked so trashy that we ended up nicknaming her Oscar The Grouch. The other girl’s name was Serena. She was gorgeous and, at the time, out of my league.

Serena was a borderline-anorexic model who used to cut herself. She smoked weed and did a lot of coke. She had long black hair and wore hoodies because she thought she was fat.

Each day after class, my friend and I would talk about how hot Serena was. She was really nice to me. She was cool and seemed approachable. One day after class I said fuck it, walked back in, and asked her for her number. Her face lit up and she said “Sure!” — I couldn’t believe it. She was the hottest girl I ever spoke to.

We ended up going to the movies a few nights later and made out in the theatre. We had a thing for a few weeks. We would drive around, talk, listen to music, and make out. She had a policy of only having sex with boyfriends. I never got the boyfriend label.

During that time, I was still bitter about my ex-girlfriend, and still angry at women. One night I said something really stupid. I don’t remember exactly what I said, but it was awkward. I probably said something off-putting about women. She stopped talking to me soon after that.

Serena and I weren’t on bad terms. We remained friends on Instagram, liked each other’s posts, and flirted when we saw each other at parties. I knew I could strike things up again, but I didn’t have the confidence. I felt like a failure for blowing it the first time. Until one day almost a decade later, in my late 20’s, we bumped into each other in SoHo. She looked incredible. I said that her and I should get a drink and catch up. She said yes. At that point, I was sleeping with multiple women and significantly more confident. I figured this should be easy. It wasn’t. We went on five dates and none of them ended with me sleeping with her. Serena gave me several attempts to try and redeem myself, but I didn’t — I fumbled the bag.