Matchmaker Claims to Have Inside Track on Love

"I really want to be in a great relationship," said Orli Ross, 33. "I want a husband, I'd like a family. I really feel I've done everything that I could possibly do up to this point. So, why not?"

Orli Ross, a 33-year-old pharmaceutical sales rep living in New York City, said she had gone through lots of relationships and every dating service out there, with no success. Then she took her search for a mate a step further.

Ross recently paid a matchmaking service $10,000 to set her up on three blind dates. It took Ross two years to save up the money. It's a high stakes version of "The Dating Game" that she believes she can't afford not to play.

Matchmaker, Matchmaker Make Me a MatchPlay

"I really want to be in a great relationship," she said. "I want a husband, I'd like a family. I really feel I've done everything that I could possibly do up to this point. So, why not?"

These are not garden-variety blind dates. These are three eligible, marriageable bachelors. Hand-picked and vetted by two high-end matchmakers.

"We are smart, we know when we meet a great man that we are going to hold on to him, we know how to pick and choose and we want to teach the women to pick and choose," said Susan Rose, who runs an "elite and discreet" service with Jennifer Heller called Rose and Heller Inc.

The matchmakers throw in a year's worth of "on-call" dating advice. But don't rush for your checkbook just yet, ladies: The waiting list is six months long (the pair do offer online dating advice at

"We will not take on any more people, we are at maximum right now," Heller said, citing the bad economy as a magnet for people in search of a stable relationship. "Because it's very labor-intensive, and it's very time-consuming. And we want to give everybody as much attention as we can. They are calling us 24/7, they have access to us. So we never shut off, we never say no."

Such attention to detail, they say, accounts for the expense.

The business model has proved to be a success, despite the hard times. The service recently raised its fees by $5,000, up to $15,000.

"We want to help people find love, and it's not just about finding that partner, it's about changing their mind-set," Heller said.

Which is no easy task. Heller and Rose might just be the hardest-working matchmakers in America, and they claim to have a 75 percent success rate.

For them, hobnobbing in hotel lobbies and throwing lavish cocktail parties is no fun and games. They're paid to be on the prowl for high-powered, successful and, in most cases, beautiful bachelors.

What is the secret?

'Greatest Dater Is Not the Greatest Mate'

"It's even before the chemistry," Heller said. "We uncover peoples' patterns. They could be out there dating for many years and think, 'I know how to do this,' but they are not getting into a relationship, something is stopping them. So we are able to identify that pattern."

But can women really be coached into attracting Mr. Right?

"Dating is really stressful," Ross said. "You go on these dates, I'm constantly out there networking. It would be nice to sort of sit back and have someone choose for me, so that's part of the reason I've invested in it."

Does Ross think she's been doing anything wrong?

"Maybe I haven't chosen correctly, and maybe the wrong guys are attracted to me, and that's why I hired Susan and Jennifer, because I really want to dig in deeper to find out what's going on," she said.

Before the dates, Ross undergoes a kind of date coaching. The first step is a grueling personal assessment.

"The man is not going to come in and swoop you up," Rose said. "That's just not going to happen."

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."

Rose elaborated.

"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."

'Would You Wear This on a Date?'

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."

Heller objected.

"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.

"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.

"What would I put in the toaster?" Ross said. "I would put toast in the toaster."

"I'm sorry," Max said. "You lose again."

"How would I lose?" Ross asked.

"Bread," Max said. "Toast is what comes out. I'm sorry -- does it not feel good to lose?"

He talked about loving travel, she confessed to hating to fly. Later, he beat her in thumb wrestling.

So, was he a winner?

"We had a great time," Max said after the scheduled date came to a close. "Dinner was wonderful, we had great conversation. No awkward moments. Things were good, and we are going to continue the night out, so things went well."

Ross rated Max's attractiveness. "My first impression wasn't like, ahhh, let me bite the buttons off his shirt, per se -- but I'm thinking that maybe, if I gave him a chance, we could consider removing the shirt, at some point," she said. "But I would have to go on three or four dates to see if that would be possible. We are going to have a drink off-camera so that maybe I can get to know him and see if maybe that 'sparkilicious' feeling can come into play."

Heller saw a chance.

"I would like to see her liking him," she said. "I think he would settle down and I think he would make a wonderful partner. And I hope she can see that. Because underneath his kind of calm demeanor, I think he is an interesting [guy], and I want her to give him a chance."

But a few weeks passed, and Ross still had had no second date with Max or John.

So the matchmakers decided to step it up a notch. Date No. 3 was Mario, a 29-year-old Italian investment banker.

"Her heart is going to go pitter patter big time for him, he is a lovely fellow," Heller said. "Handsome, sweet, interesting.

"His charismatic style just sweeps her, and she likes to be swept and that is not going to work for her in the long time. I think he is adorable. I like the charity work he does, I like that he takes his career very seriously. He is extremely charismatic, handsome, stable loving family. Values some of the same things. I think her heart will go pitter pat for him. Definitely."

Mario whisked Ross off to a cool Greek restaurant in her neighborhood. The pair sit down and toast their date. The wine flows, and so do the questions.

'I Think It's Courageous'

"So much to ask," Ross said.

"Where do we begin?" Mario said.

"Do you like pets?" Ross said. "Do you ski, are you a skier?"

"I snowboard," Mario said. "Are you a big skier?"

"I love, love, love to ski," Ross said. "Do you live alone?"

"I live alone," Mario said.

Ross asked, "Do you think the proactive approach is a good idea or do you think it's too aggressive?"

"I think it's a good idea," Mario said. "At the same time, I don't know if you can force these things. It eventually happens when you're not looking for it."

Ross disagreed. "The only time I'm not looking for it is when I'm sleeping," she said. "So I don't know if that would work for me."

The two continued to talk.

"Do you tweet, are you tweeting?" she asked.

"No, I'm actually not on Facebook or MySpace or any of that stuff."

"So," Ross said, "do you think what I'm doing is desperate?"

"No," Mario said. "I think it's courageous."

"Do you think this is the greatest date ever?" Ross asked.

Later, she asked, "So, are you asking me out on a second date?"

Mario laughed. "You caught me by surprise, I wasn't expecting that," he said.

"I'm direct," Ross said.

"You're very direct," Mario said.

Ross' open-book approach may have broken all the rules of a first date but, she said, she was just being honest.

"I don't think it's a desperate cry, I think it's only natural, and I think that women who don't vocalize it, and have the same feelings as I do, are maybe simply too afraid to admit it, or they are too proud," she said.

"But, for me, I've always been an open book with my family, friends on my dates. This is who I am, I want to find someone, and I'm going do my best to get him," she said.

The date seemed to have gone well.

"She's a very fun person to be with," Mario said afterward. "Bubbly, enjoyable. I enjoyed our conversation. It was not bland, it was not routine. So we discussed many topics and I had a good time. I would like to see her again. I hope she feels the same."

She did. "We got into a more detailed conversation than I think I've done with any first date -- I didn't mind it. I enjoyed it. I think we enjoy each other's company, I don't know."

And, as our matchmakers predicted, Ross definitely had butterflies.

"I thought Mario was very attractive," she said. "I mean he's got these hazel eyes and wavy hair, he's a good dresser, he's got that pink shirt thing, gray suit. He's got fashion. I liked his look, it worked for me. Mario is definitely hot, he's sexy, he's hot."

After $10,000 and three dates, Ross met with Heller and Rose for a debrief. But, so far, no second dates.

"Let's back up a little bit and talk about how you feel," Heller said. "Do you feel like you've made a transformation? Do you feel ... different about what you are projecting?"

"I really thought about that over the last couple of weeks," Ross said, "and the truth is, you gotta go for the good guy. You gotta go for the guy that wants you. At the end of the day, you don't go for the guy when it takes like three days to hear from them."

The three women hug and it's time to say goodbye.

"You just look radiant," Rose said. "OK, goodbye sweetie, call us, and keep us posted."

"Bye ladies," Ross said.

"Good job," Heller said. "Good job! But we gotta keep her on track. She's going to get those hot pants back out again, I just know it."

"Oh," Rose said, "don't tell me that."

'Don't Want to Miss an Opportunity'

Indeed, although Mario called for a second date, it didn't happen, and he never called back after that. Meanwhile, bachelors Nos. 1 and 2 both asked repeatedly to see Ross again, but she declined.

Was she discouraged by the experience?

"Am I disappointed ... maybe just a little bit," Ross said. "I mean, one of the guys was a little bit too old for me. The other guy was too young. [I was] not necessarily so physically attracted, and I think what the women have missed a little bit is that it has to be a little bit about chemistry. It has to be a little bit about physical attraction. They have to pay attention a little bit to age."

Was this money well spent for her?

"You know, this isn't something that I just did on the spur of the moment, like going to Saks Fifth Avenue and buying a sweater," she said. "Max shmax, Mario shmario -- whether or not it works with them, that's not the point. You want to be with a good guy, you want to be with a guy that respects you, calls you after a date, and sends you flowers.

"I can't have a moment when I'm down, because you never know who you are going to meet, you know?"

A month later, Ross had seen yet another online affair fizzle out. But she was not giving up.

"I'm not a serial dater, by any means," she told ABC. "But I have a date on Saturday, I have a date on Monday and possibly Wednesday. But after that, I think I'm going to need to take a break for a couple of days. I don't want to miss an opportunity, so I keep it rolling.

"But I think, after Wednesday, I need to stop. It's too much pressure."