Dealbreakers and Red Flags

I'm a huge fan of 30 Rock and think of Liz Lemon as my personal hero.  Remember that episode when Liz Lemon starts an offshoot show called "Dealbreakers?"  I feel like I've been living my own version of that.  Why, oh why, is there always something?

As I intimated in my last post, I recently went on dates with two very, very different men. 

The first guy was a saxophone player I met recently while performing...in a square.  Yep, it's slim pickings and I was picked up by a street performer.  That being said, he was actually a trained jazz artist and we had a lovely conversation after his performance.  The conversation was so pleasant, that I agreed to give him my number.

We went out on Sunday evening for a walk in the park.  We had absolutely nothing in common except for a shared passion for our very different sorts of work.  However, he is barely scraping by, but I am on the brink of realizing my dreams.  At one point, he stated that he wanted to kiss me, but he had recently kissed another girl and felt bad about wanting to kiss me as well.  Needless to say, red flags were going up in my head, but did I heed?  Of course not.  So we kissed, and it was nice, and then I found out he was in his late twenties.

Too many red flags...financial insecurity, multiple women, late twenties.

Dealbreaker.

Next.

The second guy was an English bloke I met at a pub downtown last week.  Sexy accent, cultured, great dresser, stable job...but seemed a bit older.  He gave me his number, which I thought was a bit odd and maybe old school.  I have a rule about that--I don't call boys.  After not calling for a day, he managed to track me down via social networking, and I relented (just slightly) and emailed him back.

Despite the red flags in my head, we went on a date on Monday.  It was one of the best dates I have been on in awhile--the wine flowed, as did the conversation for several hours.  I finally worked up enough liquid courage to ask him how old he was...totally thinking maybe late 30's...nope, 46 years old.  Divorced.  No kids and unlikely to want kids.

Fifteen years my senior (citizen).

Dealbreaker (with hesitation secondary to the great conversation and otherwise excellent connection).

Er...do I even want to know what's next?

On the one hand, my work didn't intimidate either of these guys.  On the other hand, with each date that I go on, the list of dealbreakers is expanding like the American waistline. I worry that pretty soon all that will exist in my head are exclusion criteria and there will be no inclusion criteria.  Guess all I can do is continue to charge onwards and upwards...