Adventures in the Dating Game: Part 1

By Cheryl Lavin

June 10, 2016 3 min read

Sarah has spunk. She likes men and wants to find the right one. She doesn't sit back waiting for the phone to ring; she's out there looking. She knows you have to kiss a lot of frogs before you find a good one, but she doesn't let the bad ones get her down. Here's her most recent dating story:

"I dated Kyle for a few months. He proved to be great at some things and not so good at others. He was immature. Some may chalk his immaturity up to his age — he's 31 — but I've dated other guys his age who were a bit more adult. So, we broke up. Or should I say, he broke up with me by unfriending me on Facebook. It was so childish.

"Fast forward a few months to when I met Seth on a dating site. He was still younger than me, 40, but the oldest guy I had dated thus far. His gray hair actually made him look older than me. He had a great job, was very generous, and seemingly had it all together. He'd host my kids and I every Sunday for swimming and a barbecue. Then, inexplicably, he texted me one day and said I was amazing and fabulous, and he wished me all the best, but he just couldn't handle me being such a nice person. Umm, what?

"And so, I was back to square one, wondering what was so wrong with being a decent person. Some guys told me I was everything they could imagine having in a partner, but apparently none of them really wanted that. I don't get it.

"I felt discouraged, but I wasn't completely down on men. I went back online (because I really don't know how else to meet people) and met a state trooper. We talked back and forth for a few weeks before he asked me out mid-October.

"For whatever reason, he stood me up, and I never heard from him again. That night, since I was already dressed and ready to go out, I posted an ad on Craigslist for a dinner date, and Ben responded. He said he was 32, in the Army, and not looking for a wife or a friend with benefits — just a companion to hang out with so he didn't have to do things alone. We met up at a hip wine bar and closed the place down!

"He was devastatingly handsome, extremely funny and articulate. I later found out he was an officer and a college graduate, and although he was around the same age that Kyle had been, he was light years ahead of Kyle in maturity. He had been deployed to Iraq, and that can make a man out of a boy pretty quickly. He's the first guy who ever said I was out of his league, although he clearly could've gotten any girl he wanted. After the wine bar closed, we went to a bar in his neighborhood just so we could still be together. Being the gentleman that he is, he never once suggested we go back to his place. I finally went home at 3:30 a.m."

To be continued...

What's your dating history?

Got a problem? Send it, along with your questions and rants to cheryllavinrapp@gmail.com. And check out my e-book, "Dear Cheryl: Advice from Tales from the Front."

Photo credit: Keoni Cabral

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