At the beginning of Summer, I made the decision and the suggestion to consider taking a break from online dating and try to meet people in “real life, in-person situations”. Summer has turned to Autumn and as I slowly trade my shorts for my sweaters, I’m continuing the offline mission.

A recent Friday night of mine was booked with Jackson. I met this man at Gym Bar, a Manhattan hangout complete with a pool table, televisions set to sports channels and men in outfits ranging from suits to workout attire. When it comes to meeting a diverse group of men, a gay sports bar is a sure ticket that will hopefully lead to Dateville.

Jackson definitely stood out in a crowd. With a full beard and standing at 6’5”, Jackson was an eye catcher, and a poster child for lumberjack hotness. We had a nice conversation- definitely not the flirtiest or the funniest- but it was nice conversation. Maybe it was the sparkle in his eye or maybe the hint of a Southern accent, but there was something definitely interesting about him. He asked me to dinner, and of course my answer was yes.

As I was walking on that crisp Friday night to the restaurant to meet him, I thought about our past conversation. I could remember very little…. was this a bad sign?

Jackson was every bit as handsome as I remembered. And tall… very, very tall. We sat down, ordered our meal, and the waiter walking away was our cue to begin an exciting and stimulating conversation. Within two minutes I was bored.

I made several attempts to get the conversation going. “Tell me about your job”… “What are your favorite things to do in Manhattan?”… “Any fun summer vacations?”… His answers to all were rather dull, lacking enthusiasm and personality.

It wasn’t until I asked “How long have you lived in New York?” that things got somewhat interesting. Jackson arrived in the 90’s too, and this took our conversation to Manhattan of the 90’s, which is always interesting to me. We talked about restaurants like Universal Bar and Grill and bars like Splash and Private Eyes. When I mentioned Club USA, he smiled and said that he was a bouncer there.

Figures he was a bouncer- tall, good-looking and a man of very few words.

When the waiter asked if we wanted to try one of their pumpkin spice desserts, I said no and asked for the check. We paid and left. Jackson gave me hug and headed East and I made my way Uptown. It wasn’t said, but like the cool breeze that was bringing Fall to Manhattan, it was obvious that this was in no way a love connection.

1Gr8Lesson

Dating is a lot like shopping for sweaters. Sometimes we see a wool sweater with a fantastically attractive design. It beckons us to try it on, and when we do we discover the sweater fits a little on the baggy side. Then we spot a nice blue V-neck, a total classic yet simple staple that never goes out of style.

Do we walk by the V-neck or do we give it a chance?

I wanted a date with Jackson just because he was great looking. I was guilty of trying on the amazing sweater, and at the time I made no apologies for it. I still make no apologies, even though my choice in sweater made me itch from boredom. By choosing the great looking Jackson, it made me wonder if I overlooked a sweater that might not have been as snazzy but may have been more my style.

It’s easy to get caught up in the exterior appearance of a potential date. Who wouldn’t want to walk into a party with a model or an athlete? The challenge is finding that person with the external looks that jazz us, but also with the smarts and the heart that keeps us interested.

The next time you’re “date shopping”- be it online or out in the field, keep in mind the whole package of a potential date. Maybe your future date is the snazzy sweater, or perhaps if you keep looking through the displays you’ll find that classic V-neck that’s just the right fit.