Cree and Cree dressed as Carmen

For the new show He's a Lady, airing on TBS, 11 men face a hair-raising adventure that most men would never dare. The challenge: for three weeks, they must live head to toe as ladies. The motivation: a quarter of a million dollars.

Cree, a Las Vegas entrepreneur, believes beauty is in the eye of the beholder when he becomes Carmen.

Since these gals were going to be graded on grace, good looks and glamour, there was stiletto camp, makeup and modeling lessons and the task most men loathe, shopping. Then, they had to introduce their alter egos to their friends and family. And the final challenge: swap places for 24 hours with their wives or girlfriends.

"I thought the stuff automatically got done," says Cree. "I learned so much of what goes into [my wife's] daily life and what she does for my son Jared and I every single day. Even after a long day of work."
Donnell and Donnell dressed as Raven Nightshade

Donnell, a personal trainer who always considered himself a ladies' man, is now a manly lady known as Raven Nightshade.

Donnell says he drew some of his female energy from Oprah. "I always told my wife, 'All women have an inner Oprah inside,'" Donnell says. "What I mean by that is in times of need or in trouble, or when you need to call on something, you call on [Oprah], you know? A little bit of [Oprah]. She's in school right now, so when she gets stressed out I say. 'What would Oprah do?' And it always helps her."
David and David dressed as Wynonna

David swaps his manhood for womanly curves as Wynonna and is surprised by a plus-size epiphany.

Although he is a big guy himself, David says he never knew how hard it was to be a larger woman. "Even the less, how should I put it? The less attractive of the group men? They all garnered their shares of attention where myself, you know, I, by design or by just by where I was, I was always in the back of the pack.

"I mean, it was almost like a focused lack of attention [on me,]" says David.
Michael and Michael dressed as Scarlet.

Michael goes from a good old boy to a southern bell named Scarlet.

For three weeks as the men were plucked and tweezed, they were not allowed to talk to their friends or family. Michael actually made a pretty cute woman but the experience made him appreciate his own woman, Leigh Ann, a whole lot more. During the taping of He's a Lady Michael said, "It really hurts to be here and I can't speak to her and tell her everything. How I so respect my woman and I just want to tell her in every fashion and form. There's only Leigh Ann. I want to give her everything."
Michael proposes to Leigh Ann

Michael said that the experiment made him appreciate women and love his girlfriend even more. And boy, did he have a surprise for her!

Michael: I respect Leigh Ann and care for her and love her. I just really would like for her to come up here. …For one thing, I love you more than anything in the world.

Leigh Ann: I love you, too.

Michael: I always will. I'll stand behind you on everything and from the first night I ever saw you, you stole something from me I never want back and that's my heart. Will you marry me?

Leigh Ann: Yes!
Before and After of young woman who disguised herself to be old.

Karoline is a self-described party girl from England. She desperately clings to her youth and says she is repulsed by the elderly. In a life changing experiment, Karoline agrees to come face to face with her biggest fear. Aging. For a month straight she endures a daily five and a half hours makeup job to look like she's about 73 years old.

Karoline had to move away from her friends and family and live alone in a small apartment for an entire month.She also took a job working with senior citizens and went on a weekend getaway with 3,000 older people. Eventually, Karoline began to realize they were real people with real feelings—and it changed her life.

"When I'm in the prosthetics, when I'm in the makeup, I'm older, an older version of me, but it's still me on the inside," she says. "I can kind of see the young person inside of them now. I kind of see them as just young people actually trying to deal with being old."
Daniel, a barber from London

Daniel, a barber from London, is one of few black men who actually knows what it's like to be white. Daniel conducted a radical race experiment. Through prostetics and makeup, he posed as a white man for three months.

"I was invisible all of a sudden," Daniel says. "I walked down the streets of London, and people didn't watch what I was doing, where I was in location to them, where I was in location to their pocketbook or their car. The other difference I found is when I go to shops, that's when they did look at you. They put the change in your hand rather than slam it on the counter and look to the next person. There's a difference in interaction."

Another lesson Daniel learned was not to completely hold stock in his prejudices. In disguise as a white man, Daniel went to the dog races and chatted with a kind spectator. The man was someone whom normally Daniel would have judged to be a threat for a black man. When Daniel returned later as himself, the man treated him equally as kind.

"It made me question myself," Daniel says. "I have to look about how I look at other people and how I judge a whole race or a whole group of people, and if I don't want them to do that to me, then I can't do that to them. It made me look the other way."