The following submission received third runner-up in our Stories of Woe Valentine’s Day Giveaway. Kester’s story will be performed by local improvisers, filmed, and posted on our site in the weeks to come.
Breakup breakdown
For me, the relationships have never been as bad as the breakups.
There was Kelli, the girl who wanted me to lose my virginity at 13. When I decided 13 was a bit young for that sort of thing, she seemed oaky with my decision. It wasn’t until sometime later that I realized this was because she was sleeping with other guys. When I called her on it and demanded we break up she was shocked. “I sleep with them,” she said, “because I love you!”
There was Sherry, the girl I was going to spend the rest of my life with. Until she started college while I was still in high school. One visit to see her was all it took to convince me that she was about to break it off. I beat her to the punch. Years later, hearing that she was about to be married, I drove down to San Antonio to stand outside her house like Lloyd Dahbler with a boom box and convince her to marry me instead. I never followed through.
There was DJ, who knew I was going to break up with her when I said “Can you come over? It’s important.” She showed up and we made out desperately for two hours. Afterwards, I said “I still think I want to break up.”
There was Rachel, who called me (during the same week I started shopping for engagement rings) to say she thought things were getting too serious and wanted to break up. We were best friends, so we still kept in touch the entire summer, and I played it cool the whole time.
Three months later she called and said she needed to discuss something serious. Four months later we were engaged. Nine months later we were married. Eight years later, we still are.
That last one turned out alright, I guess. The last one made them all turn out alright.
More stories of woe
- Winner: Con man
- First runner-up: High-five for love
- Second runner-up: Swingin’ surgeon Honorable mention: Blind date –>
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