Smooth Operator. NOT!

QUESTION: I've been spending time with this gentleman in my neighborhood lately. Nothing too serious, just dinner once in a while and a few "bring a date" events for my job. He wants to sleep with me and he's told me so. I'm just not ready to go to that level yet. For some reason in recent weeks though, he's felt the need to comment that he's considering sleeping with several other women. He says it to me like I'm supposed to be jealous or worried. I ignore it. And then he turns right around and asks me out on another date. What the hell is he thinking?

GARLAND: Well, lets see...

I think this guy pretty easy to read. You're not bringing him into the bed after sporting the black tie and tails for the folks at your company, so he's telling you that you aren't his franchise player. He's telling you... uh... he's TRYING to tell you that his bread is buttered on both sides.

Where are all these cheesy cliche's coming from? I'm sorry.

You're right. He wants you to be jealous - plain and simple. The only problem is, he doesn't seem bright enough to let you simmer on what he's said. If he tells you that other women are on his radar and then doesn't call you for a week, then maybe you'd reassess where your head is at - intimately - with him. All things considered, you may actually be ready to sleep with him - then again you may not! But by him boasting about other women one day and then asking you out the next, he's not really backing up his claims - which probably aren't true in the first place.

While I am usually 100% against games in relationships, I'm typically 100% for GAMESMANSHIP!

The next time he brings up these other potential lovers, snap your fingers and look at your watch and say, "You know. That reminds me of something. Can I get a raincheck for tonight? I've got somewhere to be in a little while." Then leave. Just get up and leave. If he has any sense, he'll think about what he said, and he'll wonder - just what in the heck you left to do. If he's smart, he'll feel like a jack-ass and either stop acting like he's a Smooth Operator or just sit down with you and try to talk his feelings over with you.

Either way, like I always say - at some point the two of you need to sit down and talk from the heart.

CHUCK: Here we go again. Another player of that famous game, Who Could Care Less (see a few posts back). This guy is obviously trying to make you jealous for not wanting to sleep with him, but the method by which he's going about it just seems obnoxious. Does this kind of ploy EVER work?

He wants to hang out with you, despite the lack of sexual prospects, presumably to wait you out. But he wants to give you the mistaken idea that his time is worth something, so he brings up these (possibly fanciful) relationships with other girls. Either way, this guy needs to stop playing himself, and you can help him. Like Garland suggested, you should make up your own potential boyfriend to draw him out, and see if he takes the bait.

But you need to decide whether you want to involve yourself with someone so immature that he cannot accept a relationship with you on terms other than his own. He's really not making the best case for himself right now.