Impoverished Woman, Early 20s, Seeks 'Established Man'

May 19, 2009 -- Like lovers the world over, a couple we'll call Kyle and Melissa were spending a lazy Saturday browsing local shops for something special for her. Very special, judging by the venue -- Rodeo Drive in Beverly Hills.

"Oh, look at the diamonds," Melissa cooed, eyeing a pair of stiletto pumps through the windows of the Jimmy Choo boutique. Kyle understood that meant they needed to go inside.

"This one is $1,450," said a store employee as he handed Melissa a handbag.

"OK, and this one is 15 [hundred]?" she asked, pointing to another bag. "It's so cute!"

She turned to Kyle. "It's like twice as much as we wanted to spend."

Fortunately, Melissa knew that her unambiguous taste for luxury was matched by Kyle's generosity.

Watch the story tonight on "Nightline" at 11:35 p.m. ET

Instead of the handbag, Melissa settled on a pair of $600 shoes. "I love them," she said. "I could kiss them."

"I think I'm sold," she finally said. "What do you think?"

"I'm sold," Kyle agreed.

It was only their third date, but Kyle had already spent almost $10,000 wooing Melissa (that day's haul included a ring and a bracelet from Tiffany & Co.). His unusual generosity had a simple explanation. In fact, it was a crucial step in their courtship.

"How's my hair?" Melissa asked as they strutted across Wilshire Boulevard.

Kyle looked pleased.

"Beautiful."

Kyle met Melissa on a dating Web site called "Established Men," a forum for frank talk and candid transactions where men of means are matched with stunning, young -- and oftentimes penniless -- women.

Melissa, 23, is an out-of-work actress. She could be described as a Sugar Baby.

"It's been tricky to pursue my passion because it can be feast or famine, and in the times when the work is slow, you know, you have to get another job and then that could cause you to miss auditions ... and so it is nice to be able to have a partner ... that understands where you are going and helps support that," she said.

Kyle, 42, is a divorced television producer who makes around half a million dollars a year. He's the Sugar Daddy.

"I was very skeptical about going on EstablishedMen.com," he said. "Honestly I was ... because I didn't want to feel that a girl just wanted my money and nothing else."

Melissa's arrangement with Kyle, with the ambiguous balance of money and sex it entails, is part of a growing online dating trend. Some call it practical. Others compare it with prostitution.

ABC News asked Kyle if he ever thought about whether Melissa might not find him attractive, without his money.

"You know, I always thought about that," Kyle said. "And it always bothered me. Yeah, it does. It certainly does. But on the other hand, what if I was her? And I wasn't as beautiful as she was? Would a guy like me be interested in her?

"Probably not."