MP3's A Crowd

I’ve been dating a girl for two months, and I go back and forth from thinking the relationship has legs to wanting to end it. I just had a birthday, and she got me a new iPod Touch with my name engraved on the back. I told her it was too extravagant, but she insisted I keep it. For some reason, I now want to break up with her even more, but I feel guilty about ending it after she got me this pricey gift.

—iClod

Desperation is always so sexy — like Abraham Lincoln in a lime-green mankini.

There is a natural order to things. The tennis ball does not chase the dog. (Imagine how freaked your dog would be if it did.) It also tends to go over poorly when women overtly pursue men. Males evolved to be the chasers of our species (and most other species) — to do the wooing and gift giving. Females evolved to be the choosier sex, to give men the squint-eye and wait for them to prove they are “providers.” When a woman turns the tables and does the wooing, like by giving a man an expensive present right out of the gate, the man tends to suspect there’s something wrong with her. If he wasn’t already ambivalent, he’ll likely get ambivalent. (Give a man a fish and he’ll eat for a day. Give a man you just started dating an iPod and you’ll be fishing for a new boyfriend.)

What you need to figure out is whether your “lemme outta here” feelings are about her or the fact that she got you what may seem like an iShackle. (“Hey, honey…here’s the present you’d get if we had a serious relationship — so now give me the serious relationship.”) Give this a week or two and consider whether her gift was desperation-driven or whether she maybe just got into shopping mode and, oops, went a little wild at the mall.

If you decide that your initial reaction — wanting out — is where you really stand, don’t be delayed by the price of the gift. The right time to break up is as soon as you know it’s over.If you stay with her, you might gently confide that what works best for you in a relationship is taking things slowly. We long for what’s slightly out of reach, not what’s hanging all over us raining small appliances: “I know you like music, so I’m giving you an iPod.” Your impulse: “And I know you like shoes, so I’m giving you the boot.”

A Vicious Recycle

I’m a 30-year-old single guy. Two friends from college got divorced six months ago after being married to each other for less than a year (no kids or anything). The truth is, I had a crush on the woman before they even met, and I’m fairly sure the feeling was mutual. I’d like to ask her out, but I’m certain this will bring condemnation from all our mutual “bros,” though I was never close with her husband. Does that trump the rule that you shouldn’t date a guy friend’s ex? Or is she off-limits forever?

—Wary

It’s natural to want to express your sympathy to a guy whose marriage just broke up: “Hey, man, so sorry to hear you two didn’t make it. By the way, did she happen to mention me?”

Asking out a buddy’s ex can seem like the dating version of poking your head over the booth divider at the diner and asking, “You gonna eat that?” It’s especially unseemly to forage in the remains of a guy’s relationship if he isn’t exactly skipping away from it. But assuming the Jaws of Life aren’t required to pry the guy out of the fetal position, a divorce is a breakup, not a “bent but still usable,” meaning post-divorce, it’s time for the ex-husband to release his ex-wife back into the wild.

People typically advise choosing the friend over the girl (sometimes because they think they’ll sound like bad people for advising otherwise), but you should consider what matters more to you — possibly having a crack at her or maintaining your social cred. If you do go out with her, do it discreetly at first: Go places where people won’t know you, and avoid the temptation to Facebook or live-blog your entire evening. If, after a few dates, you’re hitting it off, it’s a good idea to give the guy a heads-up via email. He might still be mad. But at least you’d just be a jerk, not a sneaky jerk. If it turns out you and she have something lasting, in time, people should begin to think of your relationship as something “meant to be” — while perhaps hiding the silver and the women when you come around.