Some lucky pieces do get a reprieve: A slightly dowdy jersey can be updated by removing the sleeves and scooping the neckline, pills can be shaved off a cashmere sweater. A gown can be refashioned into a sleek party dress. A fabulous brooch is salvaged from a little black Carmen Marc Valvo that's way too short. More often, though, the verdict is thumbs-down. A midnight blue metallic wrap dress Gayle got back in the '90s is now deemed "dated"; same for a fitted tweed jacket, and it is decided that a pair of khaki shorts Gayle calls her "Out of Africa look" should be returned to Africa—pronto!

A poufy Cinderella confection, complete with tulle skirt and satiny bodice, still fits just fine. "But it's trying too hard, Gayle," Adam explains. "You are chicer than this gown. You've moved on." Gayle tries on a floor-length milk-chocolaty brown A-line that laces up the sides. Adam stares. "You don't think this is great?" Gayle asks. "I wore it to Alicia Keys's Egyptian party." She twirls her way to the mirror. Adam circles, looks her up and down, and finally responds, "You appear to be waitressing at some sort of medieval-themed restaurant. I keep waiting for you to serve me a giant drumstick and a goblet of mead." Gayle looks to Jeffrey, who averts his eyes. She models for Kristina, who busies herself near the belts. "I love this dress," Gayle pleads. "My entire mission in life is to get rid of this dress," says Adam, refusing to budge. There is only one thing to do: Break for pizza.

After lunch everybody takes a deep breath and braces for the big bag clearance. Adam holds up a lovely malachite green Kate Spade with a large spot near the strap. "Is that bird poop?" he asks. "White hot chocolate from the airport Starbucks," Gayle answers, dropping it in the repair pile. Adam holds up four of the same tote, each in a different color, each in pristine condition. Gayle explains that they were a great deal and she got them "for bopping around." Adam tells her that they're only a great deal if you really use them. He then picks up a small evening bag that appears to be made of faux muppet. Gayle starts to laugh. "I was at a dinner party and I put this purse down near my feet and a very nice woman came over and said, 'Oh, what a darling little dog—and he's so well behaved!'" Bye-bye doggie bag. Still laughing, Gayle reaches for a handful of dried cranberries sitting on the counter as Adam asks her to focus on the better stuff. "I'd rather see you with a few quality bags than a lot of cheap ones. Out with the mock croc, in with the timeless classics." But Gayle is only half listening. "Where did we get dried cranberries?" she asks, popping two more into her mouth. "Um, Gayle," Jeffrey says quietly, "we found those in one of the bags, and we don't know how old they are. Actually," he pauses, "we don't even know that they're cranberries."

Shoes are the next Everest waiting to be scaled. In Gayle's life, clogs are a must; ditto flip-flops and slippers. Fair enough, but Adam pronounces a pair of hot pink, pointy-toed slingbacks "perfect for killing roaches in tight corners." Next Gayle slips into a Pucci pump that Adam vetoes on the grounds that it's even pointier. "Won't they ever make a comeback?" Gayle asks. "Yes," Adam says, "but the heel will have changed or something else will be altered enough that you can let these find a new place to live." Little green shoes with brown ribbon trim are cool, comfortable, and a gift from Diane Sawyer—they stay. Supersexy rhinestone stilettos that are impossible to walk in for more than six seconds at a time will be donated to the first fabulous masochist the team comes across. Charcoal gray is hard to find, so mules in that shade make the cut. After much debate, a lot of the shoes go to charity, a lot go to repair, but the vast majority stay put.

Day has turned to night. The leftover pizza has been reheated for the last time, Dancing with the Stars is winding down, and Adam opts for picking up the pace. Because Gayle doesn't own as many slacks and blouses as she does dresses, and because her resistance is starting to flag, and because she is craving a little time off for good behavior, pants and shirts are tackled with relative ease. Sweats for long plane rides and days with a head cold: keep. All but a couple of baseball caps: toss. Jeans that are a bit tight can stay. Jeans that can't be pulled past the thighs can go, and it is made very clear that "in 2012 friends don't let friends wear jeggings."

Ultimately, 152 dresses, 77 sweaters, 17 skirts, 13 coats, 12 pairs of jeans, two pairs of pants, 13 belts, 62 pairs of shoes, and 67 bags will be finding their way to other people's closets. Jeffrey and Kristina begin pulling the bags earmarked for charity out the door before Gayle can start second-guessing herself, as Adam takes a deep breath and surveys the open spaces. "You did a really good job today. You let go of more than I thought you'd ever be willing to part with," he says, exhausted but happy.


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