To date or not date....

that is the question.

In high school, I had a boyfriend. But then in college I dated my fair share of guys, but nothing serious. Then a tragic event happened my junior year of college and caused me to be pretty jaded towards guys and really never dated much after that. When I turned 30, things changed and I met the EX. Things seemed good at first but obviously again, judgement was clouded and not a grand choice in men.

So, fast forward to the fall of 2008. I met the Chef and things seem to go well. We are just so opposite and I have blogged about that before. Plus, there just doesn't seem to be a lot of effort on either part to see each other. Then there was NY Man. We click on a lot of levels and have a lot in common. BUT, he has his things that he needs to work out first and really the only way he and I could date is if he takes his time and works through those things.

So, fast forward to last night. I have known Pimp for over a year now. There is the attraction factor and he is a super nice guy. A few of us typically go out for drinks on Friday night after we close Lowe's. There has been an occasion or to where it just ends up being the girls and Pimp. Hence we changed the song My Girl to "My Pimp" one night while drinking because he is always there with the girls and it has always stuck since then. Well, last night, TMK, Pimp and I went out for one or two drinks. TMK bowed out because she had to be back at 10 am. Pimp and I ended up playing pool and closing down the bar. For the record, I still SUCK at pool. We got the closing call at 2 and closed out our tab and headed out.

Pimp and I headed out and were chatting. At some point chatting became a make out session in the parking lot. Yes - a teenager all over again. But level heads won out and I resisted the offer and headed to home to my own bed by myself. Pimp is an excellent kisser, I will give him that. :) He almost was very persuasive getting me to come over too. I just said I didn't want a drunk thing and he told me he would call tonight after he gets off from work so we could watch a movie...we'll see.

So, what is the problem one asks? Oh, about 10 years of age difference. He is much more mature than his age but freely admits he isn't ready for a serious relationship. I on the other hand feel like my biological clock is tickin. So, do you date him knowing it isn't serious until someone else comes along? Or do you pass just because the age difference? Or just date and see if it evolves into something but does that make me a cougar?

I know you silent lurkers are out there and never post, but I am expecting people to weigh in on this one. We know that I have had a terrible track record of picking guys so really not sure what to do on this one.