Dr. Phil explores the controversial trend of older women dating much younger men. Is age really just a number? First, Pie, a 58-year-old self-admitted cougar, has been dating 24-year-old Oleg for four months — and her best friend, Terese, strongly disapproves. Could Pie be headed for heartbreak?

Then, 52-year-old divorcée Bella says her relationship with 32-year-old Eddie is the best she has ever had. Eddie says he loves Bella and doesn’t mind that she’s the same age as his mother. Does this couple see a long-term future together?

And, 76-year-old Aalsa — former Miss Cougar America — says after 40, men go downhill! After dating younger men for four decades, what advice does she have for fellow cougars? Tune in and decide for yourself: Can a relationship really survive a significant age gap?

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34-Year Age Gap

Pie, 58, has been dating 24-year-old Oleg for four months. “I love younger men because one thing they have is hair. I just can’t go for the bald guys,' Pie says. "Sorry, Dr. Phil!”

Pie continues, “Based on the definition of cougar, I think I qualify. Oleg is my darling little cub right now. He’s gorgeous,” she says. “The sexual relationship is really just the icing on the cake, the whip cream on the pie. It’s just a great perk that comes along with young men. Anyone who has an issue with me going out with younger men — love is love, baby. You never know where you’re going to find it.”

“Pie is very vibrant, very alive,” Oleg says. “I like to be taken care of by my woman. I like to be pampered. Pie takes care of me. She caters to me.”

Pie’s best friend, Terese, strongly disapproves of the relationship. “What could they possibly have in common? They’re decades apart,” she says. Terese says her friend has a pattern of getting her heart broken — and she’ll have to pick up the pieces.

Oleg explains why Pie is the perfect girlfriend. And, does Pie worry about him leaving her for someone younger?

Pie explains her top tips for dating younger men.

Pie explains why she’s not interested in men her age. Dr. Phil struts his stuff to show Pie what she’s missing!

20-Year Age Gap

Bella, 52, has been dating Eddie, 32, for nearly a year. “Eddie makes me happy. Eddie makes me smile. Our chemistry is definitely off the charts.” Bella says sex with Eddie is the best she has ever had. “I love being a cougar, and I don’t care what other people think. I’m just having fun.”

Bella’s friend, Lois, says their relationship is doomed to fail. “Eddie is going to want to eventually move on to somebody younger. Once the sex is gone, he’s out the door,” she says. Lois says she worries that Eddie is a womanizer. “How do I get Bella to wake up and realize Eddie is not her future, and she’s going to get hurt in the long run?”

“My feelings for Bella are real. I don’t question it. I don’t think anyone else has a right to question it.”

Miss Cougar America

Aalsa, 76, was crowned Miss Cougar America in 2011 and says she’s been dating younger men for 40 years. “The youngest man I dated was 20, and I was 50, and he asked me out,” she says. “Younger men like me, and I like them … What do you have to lose? Certainly not your virginity!”