Heller picked up her thoughts. "And often the greatest dater is not the greatest mate," she said. "So you are looking for a great mate, not the guy who is going to take you to the coolest, hottest restaurant and the hippest party in the Hamptons, because that guy is going to fizzle."
Rose had a warning for Ross.
"It's going to be hard for you," she said. "Because we are not picking a man that you are going to be used to. We are picking a man that we think is good for you."
Ross seemed skeptical.
"For me, it's all about the chemistry," she said. "At the end of the day, you know, I have had guys that have come into my life who have been good to me to a certain degree, but I just haven't been attracted."
"Chemistry," Rose replied, "comes in all different ways. The chemistry you are presenting right now is not going to get you, you have an outfit that is going to attract a man that is thinking one thing. You need to soften yourself up and cover up a little."
Heller and Rose said they'd gotten to the root of Ross' self-destructive dating pattern.
"You know, when we asked her values, she talked about being loyal, about being kind," Heller said. "And then, over here, she's looking for Mr. Big, who is going to take her to this fancy restaurant and beach house, and out to Aspen, and where it fizzles in two weeks. So, I think she was definitely dating the fantasy and it was getting her nowhere."
"She came to us in hot pants and a very low-cut T-shirt," she said. "She wants a man, she wants a man that she is going to settle down and raise children with. I am sorry, but a man who sees that is thinking, 'hmm, I'll have a few fun nights with her but I am not going to take this woman seriously.' And we also found that Orli is always wanting to please. And she constantly wants to please so she doesn't really know what she wants."
But Ross was somewhat resistant to her highly paid advisers' advice.
"I have always been told from my friends and my family that I have really great taste in clothes, and I always wear my hair just right and my makeup is always just right and not too overdone, so I am a little, you know, hesitant" to change, she said.
The next day, it was time for the wardrobe makeover. Right off the bat, Heller and Rose said Ross was projecting the wrong image.
"Can I ask you a question?" said Rose, pointing to the short shorts Ross had on. "Would you wear this on a date?"
The answer was yes.
"I've worn this on a date -- probably like a third or fourth date -- and I get compliments on these shorts all the time," Ross said. "I work out all the time, I like to accentuate what I have."
"We are not saying to turn into somebody else, just show them the other side of you and we are not saying to change," she said. "Just calm down."
The three women rummaged through a giant pile of clothes.
But matchmaking isn't just about finding the right outfit: It's about finding the right fit. To that end, the matchmakers had interviewed one eligible, earnest, eager bachelor after another, spending weeks to narrow their list to three perfect dates.
Bachelor No. 1 was John, a 44-year-old Washington, D.C.-based political strategist. No. 2 was Max, a 29-year-old finance professional in New York City. And No. 3 was Mario, a 29-year-old Italian investment banker in New York City. None of the men wanted their last names used.
Heller handicapped John's chances.