Would You Go on a Date with An Unemployed Person?

All right, a few interesting things happened over the weekend--including a very compelling conversation I had on Friday with a friend whom I will call, for now, Dr. Love.
But let me focus, today, on last night.
Yesterday afternoon, I got a call from a guy who'd contacted me via the Internet personals. I'd just settled down to do some writing when he rang, so I said to myself, "I'll give this convo 15 minutes, tops." Instead, we ended up talking for 53 minutes. He had an incredibly sexy Eastern European accent, and was just charming and thoughtful and interesting. One of the best things he told me was about how his grandmother--who is Turkish--used to turn her cup upside down after drinking her coffee, and read people's fortunes based on the shapes that the grinds took. I love cool details like that. I love boys who talk fondly about their grandmothers.
At one point, we were talking about urban biking--he's into it, too--and I mentioned that one time, only one time, I'd taken my bike all the way over the George Washington Bridge, into New Jersey, up along the Hudson River. "It was 5 hours, round-trip, and I went by myself, and I will never, ever do anything like that again," I said.
"Part of the problem on those long bike rides, I've noticed," he said, "is that your butt starts to get sore from sitting for so long."
"No, no," I corrected. "That's never a problem for me. I have a quite well-endowed butt."
Wait a second: Had I really just said to a complete stranger I have a quite well-endowed butt?
I leapt into the middle of the awkward pause that was occurring so I could clarify: "That is not to say my tush is fat, because it's not. Just large. Or--well--not necessarily large, even--but just--my gluteal muscles are quite powerful. Which is not to say I have elephantiasis of the behind. More like a horse's hindquarters you know? Everything back there is quite ... jacked-up. Quite firm. Oh dear. Don't be scared to meet me now. I promise, it's really a perfectly nice butt."
He let one more uncomfortable moment pass before saying, with perfect timing: "As long as you don't let your butt define you."
Then we both cracked up.
I've spoken on the phone to many prospective Internet dates, and it's quite rare that I relax enough to be a complete maniac and/or to be kind that goofy; probably even more rare that a person can actually run with my maniacal behavior and add to the silliness. It felt quite good.
What felt less good: finding out he is unemployed. Worse than that, perhaps: He is trying to figure out a whole new career! And he doesn't seem to be making progress very quickly. He did investment banking for a long time, which he didn't like for a number of reasons, particularly because it was so stressful. He tried journalism for a bit, but felt like he didn't get paid enough for what he did. And so on.
But being so adrift at age 38 ! ... that sounds like trouble to me. (What do you guys think?)
When I finally said I really had to get off the phone, we talked about meeting up for a beverage. My week was looking quite busy, I told him (because it is), but I was interested in finding out what he was like in person; I suggested we could touch base on Wednesday to make a plan for the following weekend. He said sure ... but also mentioned that he could do something that very night, i.e. last night, if I was up for it.
I declined his last-minute invitation ... but around 8pm--after I'd biked back home from the gym in the heat that remained at 90 DEGREES even after the sun had gone down; after I arrived back to my apartment with its cantankerous air-conditioner, which seems incapable of cooling the air below 83 degrees, which just isn't enough relief--I decided, what the hell, I would like to go out for a cool beverage.
But I debated ever so slightly calling the boy. In the hours since we'd spoken, I'd started trying to talk myself out of getting together with him. No matter how much fun we had chatting, did I really have any kind of future with a guy who, at age 38, had no job and no career and no prospects?
I was fairly sure I didn't.
But what the hell, it was too darn hot, and I didn't have anything else to do ... so I phoned him up and I said, "If you're still free, do you want to hang?"
I arrived at the place with sidewalk umbrellas in Fort Greene where we were meeting at 10pm and there he was, waiting for me: astonishingly handsome, movie-star handsome, nerve-wrackingly handsome! (His pictures had been not so good--one with sunglasses, one that was blurry--and when I'd called him out on that, he'd said he was not photogenic but that he was fairly certain I would not be disappointed.) My first thought was: Dear God, he is out of my league! What am I doing here? I can't believe I engaged in some awkward banter about my butt earlier WITH SOMEONE WHO IS AS HOT AS HE IS!
But then I sat my extra-firm butt down in the chair, and held myself steady. We talked about serious things and not-so-serious things and all sorts of things. He had a nicely-shaped oval face, and rich swirls of dark hair. His dark eyes got enormous and round and child-like, and seemed to take up his whole face when the serious things were being discussed. But when he laughed, his face collapsed into a series of crinkles that weren't apparent otherwise, and his eyes fell to their sides, and receded backwards, but kept glimmering away, the dark pools of vision pulling you back into him.
Did I mention he was hot? He was really hot. (I am not objectifying here; part of the hotness came from his personality.) And he touched off some nurturing desire in me, an instinct I haven't felt in a while.
As for how things ended, though ... well, I'm going to hold off on telling you about that till tomorrow.
In the meantime, lovelies, tell me this: Would YOU ever go out with a guy who is unemployed? What about a guy who is unemployed AND also searching for a career? Do you think a woman shouldn't even waste her time with a person like this?
PS: Dear Edwinna, Rachel and Raye: Thanks for the support during my time of social lechery! Also, Rachel, you say confidence is a skill that can be gained: Do you have any pointers on this?
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