Halt! Don't Go There!: Places Where You Should *Never* Look for Dates

I have a pretty good crush on a guy who works out at my gym. (Yes, it's you, Rich, in case you're reading! I love you in your cute Polo T-shirts, and you know it, you wise-cracker!) ... Ahem. (Did I just say wise-cracker?) But I would never ever date...

Hello, guys. Today I want to talk about the man who is currently responsible for adding more joy to my life than any other male in the world: my gym crush, Rich. He's about 6'5, huge dark eyes, and more importantly, he always cracks me up. He called me Moses for a while, after I told him I only ate fish; and after he caught me reading Brother Karamazov on the elliptical machine, my nickname became The Intellectual. He's only 24 — but the age difference doesn't stop him from being a shameless flirt. (In fact, I should probably ask him for some tips on how it's done.) He likes to read, so he's always asking me about the books I'm toting with me. (This week, it's Ben Kunkel's Indecision.) And one day, when he asked me what kind of work I did, I mentioned that I'd written a novel of my own; since then, he likes to tease me about how he's going to move into my big new apartment overlooking the Park once I sell my book for a huge advance. (Never mind that the reality is that I'll be happy to sell my book at all in this tough economy. Fingers crossed!)

I do fantasize a little about dating Rich ... about holding hands as we stroll around the Slope ... about smooching ... even going all the way with him! ... but I'd never so much as go out for coffee with him, like he's hinted that we should do, not in a million years. That has nothing to do with his age — I am an unapologetic cradle-robber, ladies and gents. It has everything to do with his gym membership. There are few places more sacred to me than the workout facility he and I frequent. And if we got romantically involved, and it went to hell, and we got romantically uninvolved, I'd feel so uncomfortable about going to the gym that, instead, I'd sit at home every night, stuffing my face with dates and peanut-butter-and-jelly sandwiches, watching Sex and the City DVDs. And I'd turn into a fat slug, la Jabba the Hut. And no man would ever look at me again. And I'd die obese and lonely!

So, Rich, as much as I love you, my sweet, I cannot ruin my entire life for a roll in the hay with you.

And there are a few other places, besides the gym, that should be off-limits in terms of boyfriend sourcing, don't you think? A few other guys, besides the gym crush, who should be off-limits. Like:

Your fellow tenant in the place where you live.

Sure, it's convenient at first, a love affair with the hottie on the first floor ... but once it goes down the tubes, it's can be kind of awkward, as it was for my old buddy Henry. He lived above the girl he was sleeping with for a few months. After they broke up, there were a few times when she called him, saying "I can hear you up there — who are f**king? WHO IS SHE?" Scary. He was getting ready to find a new place, cheap rent be damned, when the girl rang up to report (in tears) that she was moving out, because she couldn't take it any more.

Your dentist.

Little-known fact: Dentists are party animals. A crazy friend of mine, Cassie, once dated her dentist, and they'd go out clubbing every night and snort a bunch of coke, and he bought her a diamond bracelet for their, like, one-week anniversary — and then went totally psycho on her when she tried to break it off! Wouldn't stop calling, showed up in the middle of the night banging on her door — and then she even heard from the crazy dentist's wife! (She hadn't known he was married!) ... Having heard this insane story, I declined when my own (quite adorable) dentist asked me out on a date two years ago. But the whole thing was so awkward that I haven't been able to call him for an appointment since. And my teeth are rotting! Let this be a cautionary tale to you wild kids out there: Dating the wrong kind of men (i.e., dentists!) can really put your dental hygiene at great risk.

Your shrink.

The evil stepmother of a friend of mine recently broke up with her husband — my friend's father — so she could start dating her shrink. What makes this whole story even more wrong is that she herself is an psychoanalyst! So people, Prince of Tides notwithstanding, please don't pull your therapist onto the couch with you. It's bad news when the person who is supposed to help you figure out all your psychodrama becomes the person who is creating it.

Your office-mate.

My father likes to say: Don't piss where you eat. Similarly: Don't screw where you toil. In other words: Please think carefully before you let your office-mate dip his pen in your ink well. He is someone you will have to see every single day, after all, and behave professionally in front of from 9-to-5. If you're convinced you're in love and you two will go the distance, that's one thing. (And I still might hold off till one of you gets transferred to a different department.) But going out to, say, the Corner Bistro, after work, getting wasted on shots to celebrate the end of a tough week, and then taking your co-worker home with you ... ? Probably a terrible idea. Probably not worth the potential awkwardness. (Then again, my crazy friend Cassie dated someone she used to work, and that didn't go so badly — perhaps because she got fired about two weeks after the affair started so they were free to continue their romancing without the pressures of the workplace. And you know what she and her beau did on her last day of work? They stayed later than everyone else — and then they had sex on her boss's desk! I kid you not.)

All right, my lovelies, if you have your own stories about people you SHOULDN'T date, lay 'em on me.