On Nov. 13, 2003, Wynonna was arrested for drunken driving and had a humiliating mug shot splattered across televisions and tabloids across the country. Two weeks prior to her headline-making arrest, Wynnona came to Oprah asking her for help. Wynonna told Oprah her life was out of control and that her weight was at an all-time high.
"Why am I here? Next year I celebrate 20 years of being on the road. I've dedicated my life to country music, I home school my children, I worked three years on my record, I support, you know, 40 to 50 families, I have for 18 years, and I never stopped. And I'm in trouble because I lost myself. I'm the woman who forgot to put herself on the list. And I'm real tired...I don't have it together. I'm losing my way here." — Wynonna
Wynonna says her weight problem began as a young girl, just after her parents divorced. "I had been so alone those years of my life my parents were divorced that I would get so hungry, I would get panicky." At the age of 18, she had a No. 1 record and was traveling all over the country. But food became her comfort from terrible loneliness, she says. Then, two years ago, she and her husband divorced. Today, Wynonna says she is at her heaviest.
"I keep thinking I can do it myself," Wynonna says. "And the hardest part is saying, 'I can't do it by myself.' I really thought I was so damn strong that I could. ... The other night at this function, I look at mom and Ashley who are so beautiful...I'm standing there with mom and Ashley and I feel like I don't belong. I've never felt like I belonged."
When Wynonna was 30, her mother Naomi told Wynonna a secret she had been keeping from her daughter all her life: Wynonna and her younger sister, Ashley, had different fathers. That her mother kept it from her has been very painful, Wynonna says.
"The first thing I said was, 'It's okay.' And of course I'm raging inside...and I've just now come to realize nine years later, I'm really angry. Being authentic and knowing who you are, not just what you do, is sacred and I'm doing it now, and all the work is painful."
Naomi had gotten pregnant at 17 by a young man who did not take responsibility for the child. To give Wynonna a "name," Naomi married another man. Even though Wynonna did not know about this, Ashley has known she had a different father since she was a child.
Naomi: I don't know that I thought about it every day of my life, but there were certainly very few days that I didn't live with this secret and I think it does something to a child.
Ashley: I think...not knowing the truth is what has messed her up rather than having found out. I had more compassion and understanding for her because I knew. It's interesting that I didn't consider it my place to tell her. I'm not sure why I didn't but I certainly got to the point when I was 26 when I thought, "Enough!"
Naomi: This is a new day dawning for the Judd family because as mercilessly candid as Wynonna and I have been, we've never ever talked about her core issue, which is weight...I wasn't as sympathetic as I could have been...My prayer is that she's really going to be a detective in her life and she's going to step back and ask what's going on with her emotionally when she's headed for the kitchen."
Ashley: Her current effort [to lose weight] is different because of how deeply she's investigating the roots of her extra weight and why all those previous efforts did fail. I think that doing it publicly with Oprah as her supporter will be really helpful. I hope that I've made it clear over the years, I love her however she is, as long as she's healthy.
With the help of Oprah's personal trainer, Bob Greene, Wynonna committed to improving her health.
"There are tremendous challenges—some significant work needing to be done," Bob explains. "The eating is the next horizon. There's a lot of tough work. Not everyone was necessarily meant to beat this thing. But it can be done, and it's an unbelievable journey, if you're up for it. Every day you have to recommit to working out, to this way of life. It's not easy."
Wynonna has been working with her own personal trainer, Dominick, for several years, but this is the first time he's seen her really try to change her life.
"I have [noticed a change in her commitment], and it's only because of this show," Dominick said. "I've been with her for three years, and it was always like, 'How can I get her to commit to this workout?' She's always giving to everybody else all day long. We have a set workout, but I'm always the first to get cancelled. I know in her heart, she wants this."
Increasing her exercise isn't the only thing Wynonna has focused on in her quest to lose weight—she's also concentrating on the amount of food she eats. Instead of grazing late at night, Wynonna sits down to healthy dinners prepared by her personal chef, Cathy.
"The biggest thing we're monitoring right now is Wynonna's portions," Cathy says.
It's one of the hardest parts of the change in lifestyle, Wynonna admits, because she no longer gets that instant gratification!
Bob said this new commitment would challenge your marriage. Has it?
Roach, Wynonna's husband:
I really don't see a bad challenge. I see a good challenge. A challenge of new life, of a new beginning. A challenge of living longer and really caring about you and your family. Because without her, there is no family.
He is so optimistic. Roach loves me. He's seen me at my best and worst. He is more positive than I am, and it puts a little more pressure on me. I'm trying to look at him and say, yes, I want to do this for you, but I have to do it for myself.
Look back at all the Judd family's Oprah Show appearances
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