What do you do? I’m an old-fashioned matchmaker! Well, not super old-fashioned since I have a website. I meet with singles, get to know them and then match them up with like-minded people I think they should meet.
How did you get into the matchmaking game? I’m a very social person, so in university I liked connecting friends, saying “you know, you guys should hang out”— and sometimes those turned into romances. As I got older, I started actively setting people up because I know how hard it is to meet other singles, especially in the city.
What made you turn pro? It was difficult for me to make a living strictly freelance writing, and I wanted to do something that combines all of my favourite things: talking to people, being nosy, asking questions, setting my own hours and doing some form of good in the world—as hokey as that sounds.
What sets your matchmaking services apart from apps and dating sites? I dated on sites like OKCupid and Plenty of Fish for a long time and looked into personal matchmakers for myself to get someone else to do the work for me, but they were far too expensive. The most reasonable price I found was $2,000 for a year. So I decided to start a service that costs about the same as Match.com or eHarmony, around $300 per year, but with personalized curation by an actual human being.
Why did you decide to title yourself Chief Yenta? Yenta is a Yiddish word for “meddling,” but I like to think of this as the loveliest form of meddling.
What is a typical workday for you, or does that exist? Oh man, I just laughed so hard. There’s no typical workday. A typical workweek consists of meeting with clients, doing promotions to acquire new clients, and looking through my current roster and database to see if I’ve missed any potential matches. I’m constantly trying to grow that roster because the larger it is, the better the options are for my other clients.
What is the biggest mistake people make when looking for love? Having a very rigid idea of who that person is; what they’re going to look like, what they’re going to be doing for work, how tall they’ going to be. I’m not asking people to lower their standards, but I want people to keep an open mind because maybe the person who makes you feel good and loved and who fits in your life is not the height that you thought, or maybe they don’t have all their hair, or maybe they’ve had a divorce. People have a lot of deal-breakers that close off so many options, and then they’re not open to the people who maybe could make them the happiest.
Who typically signs up for your services? The reach has been astonishing. My clientele includes people of every age, orientation, ethnicity, occupation and background. It’s as diverse as this city.
Is there anyone you won’t match for? Intolerant assholes. I have an application and sometimes people come through and sound like terrible human beings, they’re just sexist or racist. I meet with every single client in person and I’m not going to set anyone up with someone that I felt uncomfortable with.
How did your dating experience influence your work as a matchmaker? It made me a lot more empathetic towards people. It’s really disheartening to go on endless amounts of awful dates and feel like you’re never going to find anyone. My heart hurts along with people who express those frustrations. [Note: Sofi is now happily off the market. No, he wasn’t a client].
Do you ever have clients you can’t find a match for? All the time. It’s unfortunate. What I offer is a full refund at the end of one year, or I can continue to extend them on the roster until a match is found. I found that more people go for the extension instead of the refund because they understand that these things take time. It’s sad and it’s frustrating, but I can’t get the whole world paired off.
Well, if that happened, there’d be no one left to matchmake! That is true, but I’d be really happy to go out of business because everyone is in love.
What do you find challenging about being a matchmaker? The ratio between the genders. It seems a lot more women are looking for relationships than men. Women in their 30s come to me ready to find someone, but unfortunately all the men in their 30s and 40s who would be dating them are dating 25-year-olds or they’re not looking to settle down. A lot of guys are also less willing to invest money in their love lives because they have their sisters, co-workers or lady friends who want to set them up.
Are you a full-time Yenta now or do you do other things to pay the bills? I still do this in addition to writing. I’m a bi-weekly columnist for the Toronto Star and I’m working on a couple of books right now, a non-fiction dating book and a collection of short stories.
What’s the best part of your day? Whenever I get an email back from somebody after a date went really well, it’s always the greatest feeling. One of the couples I matched just got engaged and when they sent me their engagement story, I pretty much cried for an hour I was so happy.
What’s the worst part of your day? When I have to turn away women because I have like 17 women who applied in one weekend and only one guy.
If someone wanted to be a matchmaker, what qualities do they need? Empathy and intuition. You really have to understand people as individuals. Sometimes people may not see the type of matches that could be great for them and you have to trust yourself to offer options that may be a bit outside what they thought they wanted. For example, if a super passive and sweet guy really likes high energy, high-maintenance, type-A girls, I would try and talk him into meeting someone who is a little more relaxed, like him.
How do unwind after a long day? I like to read a nice CanLit-y, angsty book, like something about a family in the Prairies. I’m a romantic person, but I’m not into rom-coms or Harlequins.
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