The Case of the Fickle Friend

Dear Dategirl,I have a friend who is a 39-year-old coach and high-school teacher. He's single and has no problems attracting women, but once he gets them, he dates them four times and dumps them, always claiming he's suddenly "not attracted" to them. Then he calls me three nights a week wanting to scout talent at the bars.I'm 47, happily cohabitating, and have just about had it with this cat. What's his problem? What should I do? Do I need to dump his single ass? He's a nice guy and nice to women, but he's under some belief system that women have to be smokin' hot, young, funny and intelligent. I keep telling him that he's going to end up divorced, with kids, a nasty ex, and all sorts of financial grief if he keeps passing up available women.—Raymundo

Raymundo, it seems pretty clear that your buddy enjoys his life just the way it is. Unless there's something you're not telling me, he seems utterly uninterested in a long-term relationship. Does he cry himself to sleep every night? Soak your shoulder with lonely teardrops? Doesn't sound like it. Sounds to me like he's a coozehound and quite happy about it.Some people aren't cut out for monogamy. Better he cut these ladies loose after a few dates than keep them hanging on for months or years at a time, then showing them to the curb. You need to quit worrying about him.I understand why you find his behavior annoying—being always on the lookout for something better is a symptom of a fairly immature brain. Just this past weekend I was at an art opening, and this older (mid-60s) guy started talking to me and some friends. He decided to tell us about his 18-year-old intern's attempt to fix him up with her 45-year-old mother. We smiled politely until he started gassing on about how he'd much prefer to get with the daughter. Gross, gramps.Once you get older—and 39 qualifies—you realize there will always be someone better looking, smarter, or funnier than the person you're with. But the same works in reverse, and it doesn't sound as though your friend quite fathoms this yet. In a few years he'll realize the women he's attracting are getting older, wider, and wiser to his game. And unless he plans on making a whole lot more money, the young hotties are going to look right past him.He needs to have a little sympathy and admit that being the wingman gets old fast. I don't know about you, but when I go out to a bar with a friend it's so we can hang out together. When you're out with someone on the prowl, you're just a prop.I've been the prowler—who hasn't?—and I've also been on the sidelines. I can testify that being on the hunt is way more fun. I mean, think of the possibilities—he might wake up with a supermodel in his bed. Depending on how much you drink and how late you stay out aiding and abetting, you're most likely going to start the next day with a wicked hangover and a pissed-off spouse.Your friend needs to find more single buddies. Taken dudes don't necessarily want to be out every night pounding beers and staring at boobies they can't touch. Not many ladies are looking to be saddled with some drunk booby-watcher either.So while I don't think you have to dump your friend, you should tell him that your days of being his plus-one are over. You'll go to a hockey game, maybe share a meal or watch a band. But you're not going to be by his side while he's on his endless quest for

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