04/26/2010 05:12 am ET Updated May 25, 2011

Two's Company, Three's a Crowd

I'm sitting at dinner with a friend complaining about how I don't understand why this last relationship didn't work out when I could have sworn that I did everything right. After all, I did write the book on dating in Chicago. He bluntly responds, "Gena, it's really simple. Men are only as faithful as their options." I hate to say it, but he's right. It seems to be even more of a problem amongst online daters. You go out on a date with a guy/girl and adore them, but then come home and wonder if there is someone better out there; someone smarter, funnier, taller, and who chews with their mouth closed, for instance. You find yourself spending your weeknights trolling for dates and filling up your social calendar for weeks to come, and all the while trying to remember where each date is from, how many siblings they have and where they live in the city.

I met Jack Tripper (names have been changed to protect the not so innocent) about 8 months after moving to Chicago on At first I didn't find him very attractive and not really my type. He is goofy and not in an endearing way, has crazy wild hair, and he once mentioned that he doesn't like board games that didn't make him think. I don't know about you guys, but when my friends and I have game day, we stick with fun games like Catchphrase and Pictionary. You know, the games where we can drink copious amounts of wine while playing and still be able to slur out a clue, or stumble around trying to act it out if our words fail us. I assume we are doomed from the start, but at the time I was in between jobs and hungry, so I take him up on his offer for dinner at a Thai place in my neighborhood. We meet at the restaurant and he is exactly what I expect him to be -- dry, boring and totally nerdy. Did I mention he is wearing a Hawaiian shirt? In January? Enough said.

Halfway through dinner the strangest thing happens; he becomes really funny and I actually start enjoying his company! It is then that I decide it would be best to continue my alcohol consumption on his dime at another bar. On our way to the pub around the corner, there is a brief moment where I look at him and think to myself, "I could probably date you. I mean, I have performed miracle makeovers on other boyfriends in the past. This should be a piece of cake." In between my thoughts of what he will look like when I put product in his hair and after burning that damn shirt he is wearing, a beautiful qomN (and I mean beautiful, folks...she looked like Minka Kelly), walked over and tapped him on the shoulder. He turns around to see who it is and is greeted with a giant kiss on the lips.

At first I think this girl has to have been dared to do that. Then I think she has clearly mistaken him for someone else. You know, someone slightly less...him. Wrong again! When they are done making out in the middle of the bar, not to mention in the middle of our date, he turns to me and says, "Well this is awkward, eh?" I laugh and say, "Oh is it? I hadn't noticed." He fidgets nervously before replying, "Gena, this is my girlfriend, Kelly." My ears start ringing and I can't concentrate on anything else he is saying. My only recollection of that moment is of Minka shooting death rays at me with her eyes, and then two minutes later, feeling the cold sensation of me wearing her Bud Light all over my shirt. Apparently, Minka is a hottie, but a hottie with a serious temper.

I walk home soaking wet in the middle of January, reeking of beer and trying to rack my brain about how that man, the nerdy guy in the Hawaiian shirt, could have pulled two beautiful women and then could have been stupid enough to cheat on his out of his league girlfriend? Then it hit me. Options people. He was only as faithful as his options. Sigh.

When I look back on the date, I realize that what blows my mind more than anything isn't the fact that I left wearing the girl's beer, but more so that a man would cheat on a woman so flawless. I know I had my Chardonnay goggles on, but I didn't see a pore on her face! That weekend, I tell this story to the same friend of mine whose words of wisdom are at the beginning of this saga, and he kindly reminds me of another saying: "Show me a beautiful woman, and I'll show you a man who is tired of sleeping with her." There you have it ladies! Men are never satisfied. What else is new?