Old Dud vs. New Stud?

QUESTION: I have a friend who wants to know the following: She's met this guy who's from Israel. She's been going out with him for about 6 weeks now and they've had mediocre sex a couple of times. This guy's a little older than her and smokes, which is somewhat of a turnoff to her. The problem is, he has this really cute friend that she's been checking out and wants to approach. The friend is more her age and really stirs her juices, if you know what I mean. Should she jump ship and approach the friend, dump her lover and leave the friend alone, or keep em both?

GARLAND: SIX WEEKS + SO-SO LOVIN' + SMOKING + CUTE FRIEND = TIME TO HIT THE ROAD!!!

I think your friend needs to hit the road right now and drop old 'Smokey Joe.' The reason I say "right now" is because it's easier to break up with someone after six weeks than it is after seven weeks... and eight and nine and so on.

I think it's time to move on because there's several issues to deal with: this guy is a little older than her; the sex is mediocre; he smokes; and she's checking out his buddy. Now maybe just one issue would be okay - but there are several things here and any combination could stop anything long term between them. Most notably, the fact that she's checking out his younger pal. She's probably just enjoying the sexual variety that comes with being single and Smokey Joe isn't keeping her attention.

I say drop the current boyfriend. Tell your girl to be nice. Tell him she needs some space and she isn't ready to be in anything too serious. That's always the best break-up line. Tell her not to jump the cute guy's bones just yet! Don't dog the old boyfriend in his face, and don't cause tension between the guys. Give it some time. Suggest she make her presence [and her newfound single-ness] known to the younger friend and maybe give it a few weeks before she hooks him up!

CHUCK: I agree. Your friend should cut the old smokestack loose. If the sex ain't great, she's not into the smoking, and, most crucially, it's still early, get the hell out now. The longer she goes, the greater chance the guy is gonna develop an attachment that might make a breakup more stressful later.

However, if I were her, I wouldn't get too stuck on the idea of a future dating the sexy friend, either. Partner swaps between friends can be a risky minefield to walk. Some guys won't hesitate to go out with their buddy's exes. Some guys won't do it, out of respect to their friends. I remember having an attraction for one of my brother's ex-girlfriends that I thought was returned. But I never pursued it. Ultimately, it didn't feel right to me.

If she still wants to approach the guy, though, she needs to wait a reasonable length of time. Let's say, 6 weeks. And she should take a soft approach with the guy and not come on too strong. If everyone acts like an adult, she could end up with the guy she wants.