When Henry Met Dolly...

I was nervous about my date with Hipster Henry for three reasons:

1. I felt a bit under the weather and knew my energy would probably lagging.

2. He mentioned his interest in pop culture, fashion, media, and various hipsterish things, which had me concerned that he's looking for someone a little more Williamsburg-ish and trendy.

3. I liked him even before I met him. Yes, I broke one of the cardinal rules of internet dating (or, for that matter, all dating) and got my hopes up. But how could I not when Henry's emails made me laugh out loud and were full of such intelligence and playfulness? I would look forward to each of his rambling messages and, no matter how busy I was, make time to write him a novella of my own. We asked so many questions, went off on so many tangents, and bonded over so much minutiae, I decided it would be impossible (if not fatally cruel) for us to meet and not get along in person.

Yes, the stakes were higher than usual. Cute pictures, successful career, plus fantastic personality must equal eminent disaster, right?

He was already there when I got to the bar. Thank the lord; I hate being the one to wait. He picked a lovely lounge with a subdued, grown-up atmosphere. There were banquets in the back and the two other couples there looked like they were also on dates. Great choice, HH!

HH gave me a hug hello after I apologized for being a little late. He had a good balance of casual-but-put-together going on with an outfit that paired Converse sneakers with a velour jacket. After talking to him for a little while, I realized that HH was what all those hipsters wished they were: effortlessly cool, smart, funny, confident and successful. Yet he was all of these things without the fucking pretention that that so many of "Billyburg" kids seem to acquire (in fact, he doesn't even live in a "cool" neighborhood).

When we first sat down, I did that thing I often do at the beginning of a date when I'm still getting my bearings. I talked a bit too much, cranking up the charm and trying to be ultra-entertaining. Some time into my first glass of wine I relaxed and started acting more like a real person and less like I was auditioning for the role of HH's girlfriend.

The conversation had a natural flow to it and, just like in our emails, we went off on numerous tangents. We shared anecdotes and connected over various areas of pop culture and even poked fun at one of the couples, trying to figure out what their story was (which now makes me wonder if either couple watched us and did the same thing). As for sparkage... I don't know. HH is attractive, but I wasn't overwhelmed by a desire to pounce on him (which is good, because who knows what those two couples would have said then!). At the same time, I was curious and, had the circumstances been right, would have welcomed a let's-see-if-we-have-chemistry kiss.

Despite my pre-date jitters, any fatigue and impending-cold-like symptoms I had earlier that day were held at bay for the duration of the date.

I did feel we were getting along and would have liked to keep going. Unfortunately, HH had to be up early the next day to leave for a business trip, so he asked for the check at around 10:00pm. He apologized and said he wished he could stay out later, and I don't know if he was being polite or if he actually wished he could stay out later (do guys say stuff like that when they don't mean it?). He also paid for dinner and drinks, which is always a surprise, since I'm used to contributing something to the bill, independent woman that I am. But he insisted. Do guys pay on a date even if they're not into a girl? Some do, right?

All of this makes HH even more of a riddle, because he was so well-mannered and friendly and nice that I have no idea what he thought of me. I mean, obviously neither of us was overwhelmed by lust for each other, but the evening felt like a tip-of-the-iceberg date, where it's too soon to tell where things might lead. I enjoyed myself and would happily see him again. The question becomes whether HH is on the same page. Should I email him when he gets back from his trip or wait for him to get in touch with me? I don't want to play these silly games, but I know guys can get scared off if a girl appears too eager. Whereas I'm not eager, I'm just curious.

*sigh*

This is where it comes in handy to have a rotation. Having a date with a different guy in a few days and being in correspondence with several others takes the edge off meeting Hipster Henry. I'd like to hear from him, but it won't be the end of the world if I don't. Sometimes it's enough just to know I have options.