By Michelle Tan
February 09, 2009 12:00 PM

Even though it’s an abnormally chilly 13° outside, Wynonna Judd is making her way uphill—on foot—along a dirt road that cuts through her Leipers Fork, Tenn., farm. Trailed by her six dogs, the country superstar pauses to let a few off-road vehicles filled with friends and family zoom past her up the incline. In the past the singer might have hitched a ride—but this year Judd has resolved to make over her life, starting with her body. “Walking instead of hopping on a scooter,” says Judd. “What a concept!”

It’s just one of the many small changes Judd is making “to get healthier,” she says—and not because of public pressures to be thin. “Spending my life comparing myself to other people, that’s a dead end,” she says. “I think it’s time to get real and not hide behind the campaign of perfection.” Which is why even though Judd is the new celebrity spokeswoman for the diet drug Alli, which she started taking in September, she says, “I’m not going to discuss numbers.” But has she lost any weight so far? Judd demurs: “You will not hear me talk about that.”

What she will talk about is her growing concern for her physical well-being. In ’03, when her cholesterol put her at risk of a heart attack, the scared singer opened up for the first time about her emotional eating issues to Oprah. Three years later she checked into a treatment center for food addiction. “I was a people pleaser—I had trouble asking for what I need,” says Judd, adding, “I learned I can’t do it alone.”

Yet when it comes to her weight, Judd—who releases her new album of standards, Sing, on Feb. 3 and turns 45 in May—still seems to have a hard time accepting help. She takes Alli 30 minutes before each meal; that way the pill, which acts as a fat blocker, has time to work. In fact, an FDA-approved study found that for every 2 lbs. lost on a low-fat diet, an extra pound is lost on Alli.

The problem is, if Judd takes a pill and then eats a meal that has more than 15 grams of fat in it, she could suffer some humiliating side effects—namely, “loose” bowel movements. So she skips pills when she wants to indulge, like on nights when her mother, Naomi, invites her over for a casserole. Judd insists this flexibility will lead to weight loss success: “I can’t be part of a program that’s rigid. Let’s face it—how many times have you sat at a table and felt like you couldn’t partake because you were on some …” She mouths the word, “diet,” explaining, “I can’t even say the word!”

Judd rounds out her eating plan by “thinking ahead about my next meal, versus, ‘Well, I’ll go to a drive-through later and leave it to chance,'” she says. And at her four-bedroom house on the 1,000-acre stretch she shares with her mom and her actress sister Ashley, Judd releases her inner Top Chef. “I’m more in touch with chopping!” says Judd, who can whip up baked chicken wings for her kids Elijah, 14, and Grace, 12, from her first marriage (to ex boat salesman Arch Kelley). “I used to make cooking a big deal, but it’s really simple.”

Something else Judd no longer makes a big deal of in her house: weight, especially with Grace. “I see her struggling like most girls her age,” says Judd, who teaches her kids about portion control during their home school lessons and incorporates exercise into their daily routines. “We go out and walk—but it’s not to burn calories. With my children, I take away that obsession with how you look by doing something fun that’s going to keep them healthy.”

Their well-being became Judd’s main concern in March 2007, when she announced she filed for divorce days after her second husband, Dan Roach, was arrested for aggravated sexual battery against a minor. (Roach later pleaded guilty to a lesser offense and was sentenced to 90 days in jail.) The shocking news left Judd devastated—and determined to reprioritize her life. “When your foundation is shaken, you figure out what you need, and I need to get healthier, to be the best I can be for my kids,” she says.

Finding a new Mr. Right, however, isn’t on her radar. “I honestly haven’t gotten there yet,” she says. But she remains optimistic that love will come again. “I am living proof,” she says, “that there’s always hope.”