The Man: 60-something-year-old, a businessman in New York, N.Y.
You’re very wealthy. Tell me about why you started using a matchmaker.
I’ve repeated a lot of mistakes with women I’ve dated. They were all gorgeous, but things always ended poorly. We’re all human, despite what we say we want, in the end, we want to be with a quality person, and I’ve been attracting people who wanted my money, and not me.
Deborah is instinctively brilliant. She doesn’t treat her clients—who I’m sure are all very wealthy—as a check. My friends and I have had no issues with her. We love her.
Can you tell me a little bit more about your mistakes? What were you doing wrong?
I mean, I was just choosing young women. I could get young women to date me, and that was the wrong choice. I hung out with a lot of very well-known people, and I would date girls who wanted to feel like they were celebrities.
Tell me about your experience with your matchmaker.
She’s one of the most genuine people I know. She became a friend who I feel deeply cares about her clients. You understand someone at a deeper level when you do that, so you know how to match people better. And the women she interviews are impressive. They don’t need someone with money. They are beautiful, and have great jobs, so as you can imagine, their egos can be enormous.
And is that what you want?
Listen, in my social life, I’ve dated some extraordinary women. I’m a successful guy. And I think I’m reasonably good-looking, so I also want someone who is good-looking. But I also want someone who can be independent, and who is willing to just have an enjoyable time with me.
If you’ve dated so many extraordinary women, why do you need a matchmaker?
I’m not dependent on this. But Deborah is good at finding people. She goes into her database, or goes scouting, and looks for exactly what you want. Tall, thin blonds. Short brunettes. Good careers. Wants kids, or doesn’t want kids. You just have to be very specific, and she will ask you the right questions. Deborah takes the time to meet with you. She has dinner with you and sees how you behave, and how you might treat women. She looks at how you dress, and present yourself. She figures out if you actually want to get married, or if you’re still messing around. There is a depth and warmth about her. I felt very comfortable talking with her. That’s a credit to her.
When she figures out who you are, and finds a match for you, she just calls you up?
What she does is sends you profiles with photos, and maybe sends four of them for you to pick out. And then you work out a date. If you’re a young finance guy, or a geeky guy, she will help you with how you carry yourself, and gently bring you along. I’m older. I’ve been around the block, I’m who I am, so she doesn’t need to do that with me.
And what type of guy are you?
I’m an intellectual. I’m a downtown guy. Deborah knows that Upper East Side women would not get me. Anyone north of Houston, really. I’m a Balthazar guy. I’m a jeans guy. I like a very relaxed atmosphere, and an Upper East Side socialite is not a good match for me.
I see! Okay. So how much does Deborah charge you?
Every six months, she’ll charge about $11,000, or $13,000, and goes up to $250,000 every year. It depends on how much she’s working for you. You’re guaranteed a minimum amount of introductions, and then you pay more depending on how much more matchmaking you need.
And when I think of matchmaking, I think of something that leads to marriage, right?
Absolutely. And not just marriage material, but quality marriage material. And spending hundreds of thousands of dollars to find that person is definitely worth it to me. A guy like me—I live a very private life, and keep very few friends. If I am going to bring someone into my life, she is going to be very special.
Previously: Q+A With a Woman Who Used a Matchmaker
Photo: Flickr/Ralph and Jenny