Dating and Tequila

I went out for drinks on Monday night and had the most interesting conversation. We went to Alero in Dupont which has been the site of many an interesting conversation. I blame it on the strength of the margaritas. I swear they must pour half a bottle of tequila in them. I drank 1 and was lightheaded and then my friend ordered me another and my head started to spin. I could not even finish it.

One of the women that I was with is going through a miserable divorce. I feel terrible for her. I cannot imagine what that must be like. She is really handling it well though and is already thinking about dating again. She was asking me for dating advice. Anyone who knows me knows that is an hysterical concept. I was talking to her about online dating, and I'm pretty sure that I scared her off. It did not help that my one friend told her that she should look at men in their 60s and 70s because men in their 40s want 20 year-olds. She does have a point as I get matched online with many men in their 40s. But that does beg the question that if men in their 40s want to date 20 year-olds, what does that mean for men in their 30s or 20s? Hard to imagine that they all want jailbait.

My soon-to-be-dating friend was not so excited about this prospect. I get where she is coming from. It's hard to date someone who is a generation older than you. I know it works for some people, but I have often found it to be confusing. I once dated a guy who was 11 years older than me. That was a bit of a stretch. It became awkward when he would talk about things he did in college and I realized that I was only in elementary school at the time.

I find it really hard to date and I am childless. I cannot imagine how tough it would be to date with two small kids at home as well. However after a few drinks, I think my friend was starting to cheer up. We even defriended her soon-to-be-ex-husband from her Facebook account while we were at the table. That was a big step for her.

Ironically, I followed this evening up with a "phone date" with a guy who is in his 40s. Let's just say it was one of the most awkward conversations of all time. It's hard to talk to someone on the phone who you have never met. Small talk is much easier when you can discuss something that you are both observing in a restaurant or something. I was thinking that I should pass this guy's number along to my soon-to-be-divorced friend. They may be a better fit. However, maybe she is too "old" for him being in her 30s and all. . .