Matchmaker Claims to Have Inside Track on Love

"He looks like Michael Douglas. I think he's adorable. He's very, very, very sweet," she said. "And he is also ready to settle down. He's had serious girlfriends, he has a good track record, he also is very family oriented. And I find him very appealing."

Finally, Ross was standing outside a restaurant, ready to meet John. "I'm feeling really good, I mean I had this makeover," she told ABC. "I think Susan was a little harsh about my ponytail, but I do like my hair down, nonetheless. I'm excited. In the session, we talked about, you know, just going into it kind of in-friend mode, so that's how I want to approach it. But I am excited. I can't help it.

"They said he looked like Michael Douglas. So let's see how accurate they truly are."

John came in. "Hi," he said. "Hi," Ross replied.

The two exchanged pleasantries and sat down for a quiet, elegant meal on Manhattan's Upper West Side.

Afterward, both sides were ready to dish.

"He's a horseback rider, I'm a horseback rider," Ross said. "He's a skier, I'm a skier. I love skiing -- skiing is therapeutic to me. He's a runner, I'm a runner. There's definitely a lot of common stuff there."

John also seemed enthusiastic.

"I think the thing that struck me the most is she is so totally authentic and genuine about wanting to find a relationship and not wanting to be single," he said. "In fact, she said a couple of times that single was a dirty word for her and she didn't like it."

But did anyone feel sparks?

"I'd love to go out again," John said.

"I will definitely make that hap ... possible," Ross said. "I would love to."

One week later, Ross prepped for her second date. This time she was going out with Max, the 29-year-old finance professional. Max chose a very fancy downtown New York City restaurant known for its glittery clientele.

"He's 29, so I'm a little skeptical of age, because I typically date a smidge older," Ross said. "It feels kind of prom-y to me, because of where we are going -- we are going to Bouley, which is more upscale, more traditional, more conservative. But it's definitely an interesting restaurant choice. No, I'm excited."

Rose lobbied for Max.

"I think he's handsome," she said. "He's probably not what you are used to, but he's a real winner. If I was your age, I would be dating him in a second, he is husband material."

Ross laid out what she wanted for the date.

"I hope he's not too serious, I hope he's not too shy, I hope he's fun, I hope he comes across strong and has the qualities that I'm looking for," she said. "I know that we talked about not necessarily being swept off my feet, that's not, you know, realistic. But I hope that some of that sweeping motion, sweeping feeling, takes place, maybe just a smidge. Yeah, so we'll see."

'You're Funny, Max'

The two met and shared a toast.

"How do you feel about the fact that I'm 33?" Ross asked Max.

"Fine by me," he said. "If you don't mind a younger man."

But it soon became clear that maturity wasn't Max's strong suit.

"Say the word silk five times," he challenged Ross.

"Silk? Five times? OK, silk silk silk silk silk."

"What do cows drink?" Max asked.

"Milk," Ross answered.

"You lose," Max said. "Cows don't drink milk, they make milk. They drink water."

Between courses, Max had more riddles.

"Spell most,'" he said.

"M-o-s-t," Ross said.

"Spell roast.'"


"Spell ghost.'"

"You're funny, Max," said Ross, taking a drink of water.

"What do you put in a toaster?" Max asked.

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