When Ali Wentworth joined Oprah at the State Fair of Texas, she took on a challenge most women would never dream of—she became a Dallas Cowboys cheerleader for a day, bare midriff and all. She joined Texas' most beloved cheerleaders for a performance that she says was one of the most daring things she's ever done. "It took guts to show my gut," she says. "But as soon as you let go of your ego, I felt kind of empowered."
Watching Ali push her limits gave Oprah an idea. "I said, 'Ali, you can help so many other women who are not willing to step out of their boxes but who want to challenge themselves."
Now, Ali's spearheading a group of women who will follow in her footsteps. The Daredevils include four strangers from around the country who are bonded only by their desire to break their routines, overcome their fears and step out of their boxes.
Robin is a mother who says she feels like her life is missing something. "I have four daughters, and I want my daughters to grow up to want to be like me," she says. "Right now, I don't think they would want to."
Jane, a mother of two, lost both her job and her relationship with her husband in the past six months. "I've lost my confidence," she says. "I just need to figure out how to get it back."
Yanick, a neonatologist, says the monotony of her daily routine has gotten the best of her. "It's sometimes easier to do for others than it is to do for yourself," she says. "If your cup is empty, you can't give anyone else any water from your cup to drink."
A single mom of two boys, Melanie says her life has been paralyzed by fear."It has limited me in my choices of what I can or cannot do," she says. "I have these two brave boys who are watching their mother very carefully as they get older, and I'm not setting an example for them if I'm this scared, pathetic, weak woman."
When Ali first meets the women, she gives them each a clue about their first challenge. Fishnet stockings, a mouth guard, knee pads and fake tattoos can only mean one thing: roller derby.
Roller derby is like football on skates—women skate around a rink, and every time they pass an opponent, they score a point.
L.A. Derby Doll Alex Cohen, known in the roller derby world as "Axles of Evil," says the sport really helped her step out of her own box. "It allowed me the opportunity to see that there is nothing I can't do if I put my mind to it," she says. "This is your opportunity to bring out that part of your personality that might be lurking in here."
After a two-hour training session, Ali's team is ready for their first match. Robin says taking on her roller derby alter-ego was like rediscovering her youth. "I felt like I was 18 years old again."
The sport wasn't all light-hearted fun. Yanick says it really helped her discover her inner strength. "There's nothing I can't do," she says. "I'm more powerful than I know."
For their second challenge, Ali and her team of women arrive at another mystery location. This time, they're trading in their roller skates for parachutes because they're all going skydiving."I would rather shave my head than do this," Melanie says. The women get a lesson with veteran instructor Jim Wallace, who has made more than 21,000 jumps. "You have to have the courage when they open the door at altitude to move to the door knowing you can do this," he says. "It's a big leap of self-confidence when you step out of that aircraft."
Everyone boards the plane, but at about 10,000 feet, Melanie starts to feel sick. "I actually passed out and woke up at 12,000 feet, looked at my altimeter, and said: 'Not jumping. We're not jumping," she says. "Then he hauled me back into the plane and I threw up."
Still, Melanie says she feels the mission was a success. "I feel a lot of pride that I actually tried to do that," she says. "It's somethign I said I was never going to do and then I got that far and was willing to jump."
Despite their collective fear of heights, the rest of the women take a leap. "It was terrifying," Robin says. "But I did it."
As soon as Yanick lands, the tears start to flow. "It was just tears of release," she says. "It's every voice in my head that I inflicted that I'm not good enough. That I can't do it. Be gone. It's done; it's over."
Jane says the hardest thing about the jump was trusting her instructor. "He was a great guy, but I just don't like not having control, that feeling of just putting your life into somebody else's hands," she says.
Ali says the women had extra swagger in their steps after completing the challenge. "We walked a different walk after we jumped," she says. "I was like a superhero when I came home.... It was empowering."
For the final challenge, the women didn't wear knee pads, parachutes or...anything at all. As Ali starts to strip down on the beach for the skinny-dipping challenge, the women are all in shock. "Are you serious?" Yanick asks. "She's kidding. She's kidding."
Eventually, the women realize this is not a joking matter. Slowly, all the women but Robin run—completely naked—into the ocean. "The great thing about these three things was that you couldn't predict who was going to excel," Ali says. "I was thinking: 'There's no way Jane's going to get naked. I can just tell.' ... As soon as I showed my girls, [there's Jane], naked, running past me into the ocean."
Yanick says that of all the challenges, skinny-dipping was her greatest fear. "I'm a real woman with curves," she says. "Magazines don't say my size, you know? So naked? I mean, a month from now when I can lose 10 pounds, great. But now?"
That immediacy was the greatest thing about the challenges, Ali says. "As soon as we got over the [fear], it was like: 'Who cares what we look like? We're just going to literally get out of our skin and be a bunch of gals naked in the ocean."
After these three challenges, the women on Ali's team say they have new leases on life. Jane, whose confidence took a hit after separating from her husband and losing her job, says she got her self-esteem back. "I feel amazing," she says. "The things that I accomplished? I never in a million years ever would have thought I was jumping out of a plane unless it was crashing toward the ground on fire. And I did it. Then I realized I can do other things too that I thought I couldn't."
Robin says she finally feels like she's won the approval of her daughters. "[I wanted them to think] I'm somebody to admire, that I'm a normal woman and I didn't embarrass them," she says. "My 12-year-old welcomed me home, and it was just exciting."
For Yanick, the new rule is to take care of herself first, so she can better help others. "When you're in an airplane and the oxygen mask is going to fall down, what's the first thing they tell you? You have to put it for yourself before you can help somebody else," Yanick says. "So my mask is on. I've been trying to put my mask for everybody else. Now it's on my face. I'm back. I'm me."