DATE #11: The Non-Date, Date

This story starts like most do - almost two years ago on a flight from New York to Cincinnati. I was flying backward to Paris and he onward to California. We chatted the whole flight, exchanged names and became Facebook friends, the kind who never really spoke again.
Flash forward to this most recent February when I started this crazy mission to go on 27 dates in just about that many weeks. And this Facebook friend, unbeknown to me, was actually reading my blog. Sure it didn't happen so easily, he was really going to delete me and then discovered the humor (or patheticness of my mission) and kept reading. Then he reached out and on recent trip to New York, was brave enough to take me out.

We went for coffee and I made the plans to work around me. He didn't seem to mind. When we met up he served me the line "You're more beautiful than I remember." I was thinking, to be honest, it wasn't your looks that I remembered though it might have been the talk of fast cars and California. It was probably one of the most interesting and intriguing conversations I've ever had on a plane where usually I'm too grouchy to even acknowledge the stewardess plopping tiny bags of peanuts on my tray.

We had coffee at Le Pain Quotidien near Bryant Park. I wanted to be outside, it was a beautiful day, but something told me that would be too distracting for whatever we had to say to one another. He told me all about the date he had planned - he was going to take me sailing. Not on the Hudson but, to sail a toy boat on a pond in Central Park but in the end he was too nervous to suggest it. Then we discussed the benefit of a man who can propose a plan and make a decision. He honestly admitted it wasn't his strength. He was too easy going and probably too kind to ever suggest a woman do anything other than what she already had in mind. A part of me wishes he'd just had the courage to demand we go sailing...next time?

Our conversation then continued on the path of all the things you shouldn't say on a first date. We talked about our ex's and about their respective husbands and wives and how strange it is when there's that moment when you're no longer in their lives. And also about the secret meetings for coffee behind a spouse's back just so you can meet their baby or catch up alone and giggle about old times. Sure, it was weird date conversation but quite nice nonetheless.

We talked about how irresponsible it is of all our friends to get married and have babies and about how maybe we're both just too good to be with anyone else. Though he seems to be looking for the one, for the marriage and babies package and that could have something to do with the extra 10 years he has on me, the male biological clock or whatever.

He continuously told me how beautiful I am and how mature, how smart, sophisticated I am... it was sweet if not a little unsettling. He said he would totally tag a women like me but I am essentially out of his league. The fact that he said "tag" proves the case.

Then he tried to give me dating advice, genuinely trying to help me out I think but still...
1) Let the guy decide the date - I would if any guy could!
2) Try not to be so intimidating - as if I could help it.
3) Smile more - not a bad recommendation I guess.

Although I have no romantic interest in this fellow, I think if he lived on the east coast or I on the west, we'd probably be friends - that is at least until one of us got married.