Let Me Tell You, No Matter Your Age, Dating (Again) Is A Bitch

If you told me a year ago I would have to start the process of dating again, I'd have probably leapt off the Brooklyn Bridge and gotten it over with. For that matter, if you whispered in my ear a month ago that I'd be ready to date again in January after splitting with my partner of 10 years last September, less than four months ago, I'd probably have slapped both knees and laughed... through my tears.

The last time I went through a break-up was 1998, following seven years with my previous partner. I didn't date for a solid year, deeming it a "healing time." That's all well and good when you're in your 30s, but who wants to waste so much time again? If I intend to ever share again in the company of eligible gentlemen, I'd prefer to do it before I'm a member of AARP.

But sure enough, Wednesday evening I had a date. God, what a horrible word that is. Date. It makes me feel 16 again, and not in a good way, cool cats. Add to that: 1) It's an online meet, through an internet dating portal, which I've never ever done in my life and thus 2) It's a blind date. What the hell am I doing? I'm plenty comfortable in gay bars (not for casual pick ups), but all my single pals insist this is the way it's done in the millennium. It's worth a try, right?

After discarding one message after another and paying next to no attention to the site where I posted my profile, a couple weeks ago I heard from a man that actually appeared promising... His name was unique enough to Google his career and history... which revealed a good deal—and he came across as just that, a good deal. We exchanged messages, we talked on the phone, we agreed to meet and all seemed positive enough to proceed... with a... date. Well, shit.

And just like an overeager teen-ager, preparing for our meet Wednesday afternoon was an absurd preparatory exercise. I trimmed my eyebrows, checked my nose hairs, assessed my ears for random hair, evened up my sideburns, shaved... and then again... and once more... and trimmed my fingernails. I dabbed on my favorite Jo Malone cologne, but not too much. I put in my contacts for the first time in months; after all, working from home, I see better with glasses, but they insinuate age. That's bad, right?

And the hair... My morning "do" just didn't do. Flat. So at 3 p.m. I wet it all down again and started over. Mind you, with purported 30 mph winds Wednesday night, it ultimately made no difference. But the tousled look is good, right? Not too manicured. You know?

I was dressed by 4 p.m. for my 7 p.m. meet-up, after trying on four pairs of jeans. Do these make me look like I still have a butt at my age? Thank god I've lost 10 pounds, but does this sweater puff out too much? Is it okay to wear brown shoes with my black leather coat? Yes, this is just the occasion for my fancy Andrew Christian underwear. Okay, I think I'm ready... or not. There's no turning back now.

If you ask for my ultimate pet peeve, it's being late, so I gave myself an hour for the 35-minute subway ride. My phone is charged, I have my date's cell number in pocket... And I'm off... Exhale.

So you want to know how it went down? Pretty spectacular, actually. He is handsome, well-spoken, talkative, grown-up, confident and comfortable in his skin, inquisitive, a native New Yorker, well-dressed & groomed, pretty brown eyes and sexy. We met for drinks... and now he's not a stranger.

God, I'm glad that's over. First dates are always and forever a bitch, no matter your age. But first impression: This man seems promising. We spoke on the phone after both returning home and agreed the eve was a success, and made a second date for dinner Sunday. For our next meet, I plan to shave only once.