Continuing on my dating adventures… Last week, I went out with this guy who I went to undergrad with. I’d only seen him in passing during school and thought he was attractive but we didn’t run in the same circles so I didn’t think anything of it.

Fast forward like 10 years and I’ve run into him a few times over the past few months, once at an Urban League meeting, at a Kappa bowling party, then at The Park a few times. The last time I ran into him was during my girl’s birthday happy hour.  We had a few casual conversations but there was never much to it.  All of the ladies commented on how cute he was but something about him just seemed a little off.  Later that night, I kept the party going and went to another girl’s birthday celebration at Ben’s Next Door.  Just as I said hey to everyone, who do I spot? The guy I went to school with.

So I joke around asking him if he was stalking me. I had to crain my neck up to look at him because he’s 6’4 and I’m only 5 3-1/2″ (yes that 1/2″ makes a huge difference). Fortunately, a table opened up and we sat down and did some chatting.  The whole time he didn’t ask if I wanted a drink, but I didn’t think anything of it.  He seemed nice enough, but the girls were right something was a little awkward about him. Since he was cute and we went to the same school, I figured I give him the benefit of the doubt and accepted his offer to go out the following week.

We talked on the phone a few times and I found out he comes from a family similar to mine (parents are doing well financially, Dad’s in the Boulé , Mom’s in The Links, he grew up in Jack & Jill).  He works in the financial arena but is looking for a new job and is living with his older sister who lives in the area.  He talked about how if he couldn’t find a new job soon he’d be returning home to Chicago.  That was a turn-off because he said he’d be moving back home with his parents.  At 30, unless you’ve been laid off or have some type of illiness, living with the parents is not acceptable. 

He picked me up in DC and told me we were going to a restaurant, Cantler’s Riverside Inn, which is in the middle of nowhere in Annapolis but on the water so the view was very nice.  I gave him points for being creative in his choice of place but being in a car with someone you barely know for like an hour isn’t the ideal.  When we finally got there, I was able to take in his entire outfit.  All I could think was he looked a “Hot Mess”.  I know he’s tall but that’s no excuse for wearing ill-fitting clothing.  I tried to look beyond the clothing, I really did.  When he referred to someone as being a “bama” I had to say stop the presses.  When he told me he shops at Syms, I was done.  Hey, I would’ve at least accepted Sears or JC Penny but Syms, come on now.

The conversation over dinner could be described as interesting, at best. I watched him devour his seafood platter and I knew I couldn’t finish mine so I offered it to him, which he also quickly demolished.  Shortly after, we headed back into the city, shared a quick hug and said our goodnights. There were definitely no sparks, looks like yet another one date wonder.  My take away from that date was looks can be deceiving and they can only take you so far.  On to the next…