The Bad Date Chronicles – Sloppy Seconds Edition

As far as first dates go, “Don” and I had a pretty fabulous time.  We met on OK Cupid and traded sufficiently witty emails and text messages for a few days before he asked me out to dinner the following week.  He made reservations at a cute little place just blocks away from the studio where I take my weekly dance class so that it would be most convenient for me to meet him there.

Don marked a milestone for me – my first foray into dating someone in their 40’s.  Up until now, my dating diet had consisted of a steady supply of boys in their mid-twenties, or Snickers as I like to call them.  Because they really, really satisfy you as the old jingle says.  But we all know what happens when we eat too much junk food.  System gets all clogged up.  What I was looking for was a serious dose of fiber.  A nice big bunch of broccoli.  Don was my broccoli.  I know.  Not the most romantic notion of all time but lately I had been finding older men attractive.

They were everywhere – hot dads with babies strapped to their backs, silver foxes all dressed up for work in crisp suits, aging bearded hipsters on bicycles.  And I wanted one!  I actually wanted to date someone my own age or – gasp! – older.  Not because it was the “right” thing to do, but because, all of a sudden, I found them attractive!  I changed my age requirements online from 25-29 to 28-44.  I was very pleasantly surprised at the number and attractiveness of all the older dudes in my area.  It was time to give it a try.

Dinner was delicious, and the conversation was fun, a bit flirty and relaxing.  We traded battle stories about our dating experiences, and laughed at the overabundance of Machu Picchu pictures online.  (Apparently this happens just as often in female profiles.  Who knew?).  We even delved into our marriages and post-marriage relationships.  Before I knew it, 3 hours had flown by and he walked me to my car.  The kiss goodnight was great.  Serious chemistry.  He even asked me out for a second date!  It was damn near perfect.

The next day  I was giving my bestie all the details about the date when she stopped me mid-sentence.

Do I really want to be the Kelly in this situation?

Something about all the information I was giving her, his age, the part of town he lived in rang some bells for her.  With every new detail I gave her, she became more and more convinced that he had been the guy that a friend of hers had a short-lived relationship with the year before.  A friend that, like me, was a single mom.  There were a few questionable things about this guy, who she had met on one occasion, but nothing that really felt like a deal breaker to me.  Besides, I wasn’t close friends with this girl, although I did know her from high school.  There was only one way to be sure – ask him an oddly specific question about his favorite small mammal.

I sent him a text asking him if he was fond a certain small mammal, to which he responded, in essence, “how the hell did you know that?”  At this point, I viewed this as just a random, crazy coincidence.  One that we would be a hilarious story that we would share on our fabulous second date.  I wasn’t thrilled that I knew his ex-girlfriend (which would make dinner parties pretty weird) but I wasn’t about to let such a fabulous first date end at nothing because of it.

This is about the time the crazy train went off the rails.  His response to this coincidence was to make some petty and inappropriate comments about this girl.  I knew that she had been the one to break things off with him and it was obvious that he was still not over it.  How do I know this?  He referenced that they broke up “A year ago this week.”  He also trashed her ex-husband, who, admittedly was a scoundrel but it felt weird and just plain wrong for him to be talking to me about it.

Even though this started out with such potential and crashed and burned in spectacular fashion, I’m not giving up on older men.  In fact, I’ve got a couple more lined up.

P.S. – Big ups to my bestie (who I know is reading this) for doing such great detective work and sparing me from what would probably have been a whole barrel of fuckery.