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The Insensitive Woman's Holiday Gift Guide

Listen up, girls: Give your man an overdue makeover

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The mystical powers of that second X-chromosome have been the subject of lore since the dawn of time. Like a lioness drawn to a flailing antelope, we women seem to possess an internal radar attuned to scouting out a sale, a child with a scraped knee, or an occasion to present someone with a flawlessly appropriate gift. Everyone knows that girl who secretly plans a trip to Costa Rica for her boyfriend's birthday, replete with a handmade card and a lovers' breakfast served by natives in a rainforest bungalow. Undoubtedly, she elicited the help of his co-workers in pulling off the surprise. The office consensus is that John has an awesome girlfriend.

Women like her make the rest of us look bad.

In truth, the fairer sex isn't born with superhuman genetic abilities. Some of us have the maternal instincts of a concrete pylon and a shopping sense guided entirely by helpful pop-up ads on Martha Stewart's website. Women do, however, share one indisputable quality: We are strategists. We are Big Picture Thinkers. Always scheming, we live in a universe where nothing is left up to the gods of fate. Your neighbor, for instance, plans to cook a five-course meal for her betrothed after work. A selfless act of generosity? Please. She just wants to get laid without a rerun of South Park blaring in the background.

Whether they admit it or not, women are embattled in a constant campaign to change things they don't like about the men in their life. Some things (see: cheeky secretary) are harder than others. But for those everyday annoyances—the wardrobe faux pas, or stack of Billy Joel CDs, or other petty grievance you'd be considered a bitch for tinkering with any other day of the year—Christmas provides a golden occasion to alter his hapless ways. If you do it right, you'll earn his unsuspecting admiration as a maverick in the art of gift-giving. And indeed you are. Where would he be without your flawless guidance?

Like everything, a successful yuletide intervention comes down to planning, as in knowing when to storm the beach at the exact moment the artillery abandons post to spend 15 minutes in the john with a nudie magazine. The front: his closet. The distraction: the charitable air of Christmas spirit.

Start stealthily in the weeks leading up to the holidays, conducting search-and-extract missions for fashion offenders whose absence will generally go unnoticed. Mismatched dress socks, holey t-shirts, the festive sweater from Mom with the tags still attached—all silent casualties. Guys are notorious hoarders of anything that recalls the inebriated utopia of college life, so certain items require a more delicate approach. Collect the Nattie-stained Sig Ep sweatshirt and the baseball hat so dirty it grew legs three years ago. Pitch him your most earnest plea about the plight of the unfortunate, how the Salvation Army desperately needs him on board. Jesus wants you to donate this sweatshirt, man. You can even glean inspiration from the Pentagon's top brass and manipulate the facts. Moths are planning a catastrophic invasion of these green woolen golf pants, and we must launch a preemptive strike to save the closet's vulnerable residents. Trust me, they'll greet us as liberators.

Thus arises a bulletproof opportunity to replace the deposed with your choice of cashmere sweaters, Armani tees and dress shirts that aren't threadbare in the elbows, coupled with an Esquire subscription to provide a year's worth of fashionable propaganda.

Navigating the waters of personal grooming is dicier, if not a tad more unethical. True, guys love to be pampered, particularly if there's no chance of their buddies finding out they love to be pampered. Book a day at the spa and tag along for the bonding experience of a couples massage. Then slip a five-note to the shampoo girl to apply a tiny medallion of hot wax to the Frida Kahlo-Grizzly Adams hybrid of stray hairs between his brows and—riiiiip—problem solved. This tactic is not recommended for other areas you might want to tidy up.

We also don't suggest offhand comments about your Navy SEAL ex-boyfriend while fondling your man's pudgy bacon gut. Nothing would make you happier than seeing him suit up for a 6 a.m. jog instead of reaching for a second doughnut. But gifting a gym membership is also tricky. There's the obvious "you think I'm a fat-ass" factor, plus the squabbles that will inevitably arise when he spends the afternoon napping instead of utilizing said membership. So buy a series of boxing or rock-climbing sessions, ideally scheduled for when he's most lethargic and in the way—Saturday college-football marathons, say. But don't interfere with when his team plays. Coincidental fitness classes, paired with the favorite UT hat you gave to Goodwill, might tip him off to your surreptitious intentions.

In the meantime, wrap up those sexy new boxer briefs—and while you're at it, doodle some hearts on the nametag. Rome wasn't built in a day. Neither is the perfect man.

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