Sex & the Single Woman: The Two-Timer

All week we will be posting stories from Sex & the Single Woman’s Worst Boyfriend Of All Time contest. The winner with the most comments (minimum 5) wins a Breakup Gram from Girlfriend Grams. Start voting now, or email to share your own bad boyfriend story!

When I first moved to California, I was hit on (no, preyed on really) by my roommate’s college friend, a guy who seemed fun and successful and liked to travel. He wined and dined me, took me on fun weekend vacations, even planned a trip for us to go to Maui. He made a lot of money and went out of town a lot. For instance, he prepped me for 2 weeks for trips he was taking to London and Boston.  He emailed me from these trips, telling me about the weather, museums he went to, clubs, restaurants, etc. Except, as it turned out, he never went to either place! He actually went to Miami and to the Caribbean to visit his other girlfriend, who was going to medical school in the Virgin Islands.

Two other trips he did take, to Tahoe and New York, she accompanied him on. I first got suspicious when there were no photos taken on any of these trips (he’d claim his camera broke). Finally, he got busted when the other girlfriend posted a photo of them at the club Marquee in NYC. He tried to tell me it was a dive bar in San Diego, and taken a long time ago, but I recognized the club’s décor and the brand-new shirt he was wearing.

twotimerAfter I called him out in all his lies (and there were so many; he’d bought us both the same watch for our October birthdays, he had two cell phones, and there were other girls), I told him never to waste one more minute of my life. I heard from him only once more, at 2 am, when he called and was literally shocked that I didn’t recognize his voice and had deleted his number.

Best part—the other girl stayed with him, despite me telling her everything. Good luck to them!

PS, I eBayed the watch and got $300 for it. Ha!

The lesson I learned was to always trust your gut; when something feels like a lie, it’s probably because it is. Also, it made me appreciate my ex-boyfriend, whom I got back together with 6 months later. That guy’s loyalty and unselfishness and willingness to put me first suddenly felt so wonderful and real.