The Hustle of a Matchmaker in New York

by Grace Bello

Amy Van Doran is a matchmaker. We talked about what her job is, how she makes money from it, and common mistakes that people make when they’re trying to find love.

So you are a matchmaker. Why don’t you tell me about how your style of matchmaking is different from The Millionaire Matchmaker?
What I do is different because, historically, whenever someone hires a matchmaker, the first question people ask themselves is, “What’s wrong with this person?” or “Why can’t they find love on their own?” And so for me, I don’t think of being single as being indicative of anything being wrong with the person.

So, rather, I’m working with what I find to be the most interesting people in New York. So if you’re thinking of a pyramid, it’s that top one percent who have their shit together; who are intellectually, spiritually, and creatively and professionally very well developed; who are also good-looking. And I think that when you have everything going for you, when you’re really well-developed as a human being, I think that the population that’s available to date is also very small. It can be frustrating going online; there’s the masses to sort through, and it’s super time-consuming. So I’m catering to people that I think are amazing. I think of myself as kind of a wine connoisseur — but for people.

What kinds of fascinating, interesting people are your clients?
My clients are men and women. My youngest client right now is 26. My oldest client is 74. But typically, it’s people that are, like, creative directors of major fashion companies, people who are in tech startups, fashion designers, people in bands. For me, a dream client would be someone like Lady Gaga.

How does matchmaking work, exactly?
I only work with between twelve to fourteen people at a time. I’m actually the most affordable matchmaker, I think, in New York City at the moment. My rates start at $5,000 for six months, minimum. And it just depends on how much help they need. Do they want me to manage their online profiles? Do they want me to take new pictures for them? Do they need me to take them shopping? Are they so busy that they don’t have time to set [up] the dates or to curate the dates? So, basically, my clients outsource that entire part of their life to me.

My clients pay me, and I interview anybody who I think might be a good match. It’s free to be matched with my clients. So you can get into my Rolodex, and then I have that information, so once I have this amazing person that’s looking to meet with you, then I can just hook them up with you.

And for people who can’t afford to work with a matchmaker but they might want some help, I definitely do wingladying. I coach people to make them less shy so that they have the skill set to talk to strangers. And also, I take people shopping and help people figure out their own personal style — figure out their “marketing.” As soon as people can be specific about who they are, then the right match can more easily spot them and naturally gravitate towards them.

So how did you get into matchmaking? What did you study in school, or what was your path?
It was a weird path for me. I studied acting in college. And then, out of college, I worked in fashion. So a lot of the guys I was helping with image consulting, they were single and they wanted to meet people. So they actually would offer, like, “Hey, if you could help me meet a girl, I would pay you for that because I know that’s going to take time.” So matchmaking was a job that found me. I’m the only matchmaker that’s working with this specific subset of people. And so people find me and they ask to work with me — as opposed to me knocking down doors trying to find work. So the trick is to do something that nobody else is doing.

So what kind of stuff do you spend the most money on for your business? What kinds of expenses do you have?
For me, my expenses are low. I started this business without having any money. Most of my expenses are social-based: going out to bars, taking clients out to different social clubs or events, going to charity events to meet people. Because, basically, it’s my job to know a lot of people.

Any other expenses?
Conferences are an initial upfront expense, but if you get one client at a conference, then you end up breaking even. Other expenses would be my [shared] workspace where my clients can come meet me. Having a website designer is an expense. Anyone that can do their own web development stuff, that’s a great way to save money. Contracts, lawyers, that’s expensive.

And do you do any paid speaking engagements or anything?
Yeah, I’m always taking on consulting jobs. I’ve done close to 10,000 hours of online dating for other people, so I’ll consult with different online dating websites.

If someone can’t afford matchmaking, I will come on as an image consultant, so I’ll help someone just build an awesome online profile and take a cool picture for them and help them get together an outfit. So that’s another way that I make money.

Actually, the way I started my business is, I was helping my friends meet people. And so the first party I threw was called Date My Friends. So for $10, you could go to a party and meet 60 of my friends. And typically at these parties, people would end up meeting people. So instead of paying a matchmaker $5,000, if you can’t afford that, just come to one of my parties, and tickets are between $10 and $25. And it’s a very vetted, well-curated crowd of people you’d actually want to meet. But even if you don’t fall in love, it’s a really great way to make professional connections because most of my world is definitely the creative professional world.

And do you ever end up hooking people up with jobs?
Oh my God, constantly! I think I find people just as many jobs. And I end up inadvertently selling a lot of art. I’m getting paid for matchmaking, but because it’s my job to know people, people are always sending me leads to different things. For me, I just love connecting all the dots.

And do you make a commission out of helping someone out with their job search or selling their art?
If I was more of a staunch businesswoman, that would definitely be a possibility. But my friend, the other day, I sold some art, so she took me to Hooters as a thank you. As much as making money is important, I think the reason why people keep coming back to me is because they understand that I’m genuinely in it because I love enhancing people’s lives and making their lives better. So I’m not super motivated by money, which is probably why I’m not wealthy.

So you’ve had about 100 clients or so. Do you see any common dating mistakes that men and women make?
Yeah, actually there was an article in the Times that I was reading today…Everyone has these patterns, right? So we’re hitting the wall over and over again and expecting different results from doing the same thing. So I think a lot of people are locked into patterns. I think the most beneficial thing you can do is, if you don’t have a matchmaker, do the opposite of what you’ve been doing before to see how people are responding to you differently. So if you’ve been shy in the past, how can you shock your system into becoming a more open person? If you’re searching for one thing online and guys aren’t clicking on you, why don’t you just try searching for something different or opening up your search? And all of your friends have friends; if each one of your friends introduced you to one male friend — how can you use your resources and open up the search more?

In terms of the New York City dating scene, do you have any advice for people trying to date in New York? Because New York is such a special case. There are more women than men, people tend to be more successful here. Any unique challenges?
Yeah, I think there’s a couple of big challenges that I’ve observed. The hardest group for whom to find love is the successful, beautiful women in New York who are in their 40s. Think Miranda from Sex and the City. These are the girls who spent their 30s focusing on their careers, and it ended up paying off. And they want to meet somebody. But the problem is that they want to meet somebody that’s as successful as them. But their male peers are not always motivated to find somebody who has the same career achievements as them; [men] are more motivated to find somebody who’s younger or sexier. So these male peers are dating someone maybe ten years younger than them. But the women are looking for their equal, I guess.

As far as the professional woman, the other thing is that she’s so used to running her business or she’s so focused on achievement stuff — but what they don’t understand is that the attributes that brought them success in their workplace are not going to be the same attributes that will bring them success in the dating arena.

So, yeah, the Miranda, it’s hard for her to meet guys because the men will be intimidated. It’s hard for her to meet guys because she’s super busy, and so maybe she’s very quick, and she doesn’t have enough patience to nourish the communication that would need to go — or the time that would need to go into a relationship. A lot of what I focus on with my successful, professional women clients is how to come back into that soft femininity that typically, unfortunately, tends to attract men. So a trick would be — oh, I can’t talk about the tricks!

Is this, like, the female version of The Game?
No, no! None of that. Just, making sure before you go on a date to go home first, maybe change into a dress. And reset from the stress of the day so that you’re not carrying your work stress with you on the date. One of my matchmaker friends says, “Have the Boss Lady take off her underwear before going on the date.” And that’s, like, her little secret. She’s not going to let anybody know she’s not wearing any underwear, but when she’s sitting down at dinner, she’ll have a secret that will kind of…I don’t know. It sounds ridiculous, but I think it’s funny enough to work.

Anything else about New York dating in particular?
I also think that New Yorkers are “busy.” Even when we’re not busy, we love to say that we’re busy. I think that’s a huge turnoff. If romance is important to you, you have to make time for it, because it is the most unappealing thing in the world to think that someone doesn’t have the time or the space to nourish a relationship. I mean, everyone’s “busy” — we have to work so much to pay for our rent. But whenever you go on your dates, try to figure out how to slow things down and be focused and calm. Act like you have all the time in the world.

Grace Bello is a lifestyle and culture reporter based in New York. Follow her on Twitter @grace_land.

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