Cougar Craze: Nightclub

"This event is very simple. It's a speed date for ultra-wealthy women," says Jeremy, the organizer of Sugar Mamas and Boy Toys.


Nancy, 50, makes small talk with a potential suitor at the event. "Can I ask how old you are?" she asks.

"I'm just a baby. I'm 23," the young man replies.

"You could be my son!" she shrieks.

"A sugar mama is a woman who is horny, experienced and willing to pay," says one participant.

"I'm really open to whatever comes my way. Am I comfortable with her paying? Absolutely!" says another man.

Jeremy explains what he believes to be the mindset of young men looking for older ladies. "Finding a sugar mama is the ultimate conquest. It's not a hot girl at the bar. This is a refined woman with money who can take care of you."

"I look great for my age, and I'm successful," says Gail, 44. "I'm not ashamed of it. I usually look for someone younger only because they haven't been married and usually don't have kids."

"Men my age are stuck in a rut. They're set in their ways. My friends are, like, ‘Oh, Nancy, this is an opportunity to possibly meet someone and have sex with,'" Nancy says.

After the event, the babes and boy toys reflect on their experiences. 


"I guess being a mother, you start feeling a little maternal," Nancy says.

"I prefer older women. I realize that younger girls are just too immature," says one man.

"They were actually a lot older than I
thought they would be, I would say at least 45 to 55," says another participant. Yet he admits to scoring a few phone numbers.

"All the guys are charming, witty, funny, smart," says Gail. "Where it goes, you don't know. It certainly beats a bar!"

"How did you wind up signed up for this?" Dr. Phil asks Gail.

"All the candidates were screened, Dr. Phil. They were all under 35, but every single guy was educated," she answers. "They were all in suits. They were all well-mannered."

"Did you meet anybody you liked?"

"There were a couple of men that I think, as a friend and on a professional level, absolutely. They were 35 years old."

"But you didn't go there to make friends or find colleagues," Dr. Phil points out. "You went there to find somebody to date, right?"

"Absolutely, but I also believe that being someone's friend, or possibly a colleague, is always a wonderful way to start a relationship," Gail responds.

Nancy gives her take on the evening. "If you're asking if I met someone, unfortunately, not in that situation," she tells Dr. Phil.

"You said you actually wound up feeling kind of maternal to them," Dr. Phil notes.

"Yes, the younger ones."

Jeremy explains why he organized the meet-up. "We ended up getting in touch with the women before, and we said, ‘What is sexy to you? What is attractive to you?' And all the women said, ‘I want a younger, successful, attractive man who is also independent. He's just younger. He's someone I can get in touch with my youth with,'" he says.

"You said younger men who get involved with older women, that is ‘the ultimate fantasy, the ultimate conquest,'" Dr. Phil says. 

"Yes," Jeremy replies. 

Dr. Phil addresses Gail and Nancy. "Is that offensive to y'all's sensibilities, if that's the mindset? Certainly, that's his mindset."

"I would say that's his mindset, and it might be some men's mindset. I believe that today I see women who are younger than ever. They look better in their 40s, and 50s and 60s than they ever did," Gail replies. "I don't think they should be ashamed of who they are and what they believe in, and if they fall in love with someone who is five years, or 10 years or 15 years younger, I'm here to tell women, it's OK. Embrace it. Don't be afraid of it. Don't be afraid of who you are as a woman."

"You said that the reason this is the ultimate fantasy, the ultimate conquest, you said you have to really be confident to pleasure an older woman," Dr. Phil reminds Jeremy. 

"Yeah, because she knows what she wants " in life and in the bedroom."

"Is it all about sex?" Dr. Phil probes. "Because you talk about ‘pleasuring,' ‘conquest,' ‘fantasy.' That seems, to me, to be very one dimensional."

"You have to keep up with a woman who knows what she wants in life. When you're with a woman in her 20s, she doesn't really know what she wants in life," Jeremy says. He believes an older woman is more confident and in control. "She knows what she wants, and you have to play that part."

"Gee, you know a lot about women," Dr. Phil quips. "You had a relationship with an older woman. You said it was the best sex you'd ever had."

"I don't know if that was the direct quote."

"Actually, it is," Dr. Phil says. "You actually said it was the hottest sex you'd ever had."

"That doesn't necessarily mean it's the best," Jeremy says. "First of all, I want to say that I'm currently in a very solid relationship with a woman my own age whom I love very much. I think going back to why it is the ultimate fantasy is because the woman I was with looked at me in a different way than somebody my own age would. She looked at me and said, again, ‘I know what I want from you,' and I was in a different position than I'd ever been in."


"That's more about flexibility, apparently," Dr. Phil deadpans.

"I consider myself still a romanticist and a little on the conservative side, but I just feel that it's possible to meet someone who's younger and fall in love," Nancy tells Dr. Phil.

"I do not chase the men. I do not believe in the term 'cougar,'" Gail says.

"Is that offensive to you, the term cougar?" Dr. Phil inquires.

"I think so, because I believe today the men that I meet ask me out. I do not chase them down," Gail answers.

"When you read about cougars, it says their ‘victims' are usually younger," Dr. Phil says. "I don't get that."

"Even the terminology of ‘boy toy,' I find all those terms very offensive," Nancy says.

"I only go for men who are successful in their own right, and many of them are more successful than I am on Wall Street. They just happen to be six or seven years younger. The reason that I'm here is for you to try to help women understand each person, where their own personal comfort zone is," Gail says.

"Well, 44 doesn't seem old from where I sit," Dr. Phil says.