There’s a particular Christmas I’ll never forget—not for the usual warm and fuzzy holiday memories, but for how wildly out of hand my dating life had gotten. Fresh off a two-year dry spell, it seemed like my luck had turned overnight. Suddenly, I wasn’t just dating—I was juggling.
Heading into the holidays, I was seeing three different women, and none of them had a clue about the others. It was thrilling, chaotic, and, looking back, downright irresponsible. One weekend in particular stands out. I went on separate dates with all three—dinners, thoughtful gift exchanges, and yes, ending up at each other’s places.
I’d never felt more like a playboy, but there was one night that really pushed the limits of my “naughty or nice” list. After a date with one woman that ended in amazing sex at her place, I turned right around and went on another date—with a different woman—and repeated the process. It was reckless and exhilarating, and in the moment, I thought I was untouchable.
Christmas that year was amazing. I was living in the moment, soaking up the attention and affection from different woman with unique styles in lovemaking. But as the year wound down, reality set in. New Year’s Eve was looming, and I had to make a choice. You can’t have three dates lined up for the countdown, after all.
In the end, I chose one. Did I handle the situation perfectly? Absolutely not. But that Christmas stands out as a reminder of just how messy—and fun—life can get when you’re playing with fire.
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