Meet the Millennial New Yorker Who's Making Matchmaking Cool Again

Finding love in New York City is often overwhelming, and the online dating world is full of games. 

Next time you’re frustrated with your love life, or lack thereof, consider enlisting Hannah Orenstein as your very own millennial matchmaker.

Her newsletter, “Playing with Matches,” is a weekly digest of delightful, single New Yorkers ages 21-35. 

“Playing with Matches” is only three months old, but Orenstein has plenty of expertise to share. She’s also the Assistant Features Editor at, where she writes about pop culture, relationships, and sex ed.

Read what she has to say about the matchmaking business, first dates in New York City, and her forthcoming novel to be published by Touchstone Books, an imprint of Simon & Schuster. 

How did you get into matchmaking?


Hannah Orenstein: I grew up in Boston, and there’s this amazing magazine that comes out every Sunday with The Boston Globe and there’s a column called “Dinner with Cupid.” Every week two people are set up on a blind date. Afterward, they're interviewed and their interviews are published. Every Sunday, I'd read it with my dad, and it became a beloved family tradition.

My sophomore year of college, I joined my blog on campus called NYU Local, and I'd write stories about entertainment and talk about the city, so I thought it would be really fun to write a Cupid-style dating column for NYU Local. 

For about a year, I wrote a column called “Now Kiss,” set up NYU students on blind dates, and called them afterward. I set up my ex-boyfriend with another girl for a story for xoJane. And I realized that people were really responding to these blind date stories, it was something that I really enjoyed.

In the fall when I was a junior, I was interning at ELLE Magazine, and I did a project for E. Jean Carroll. She’s the advice columnist for ELLE, and she also has a business called Tawkify, which is a dating service. 

I was totally in love with E. Jean’s work, she really inspired me, and after I did a project for her, I sent her an email and was like, “Hey, I know you’re a matchmaker. I’m a matchmaker too.” Almost 30 seconds after I sent that, she wrote back to me and asked when she could hire me. 


I was 20 years old. I was going to go off for the semester to study abroad, but when I came back and moved back to New York for the summer, I worked for her and started matchmaking. I was a professional matchmaker with Tawkify for that year and then I kind of left matchmaking to go back to editorial because I missed writing. 

Obviously, I couldn’t let go of the idea of matchmaking. That’s how I started my novel, Playing with Matches, and I still do it on the side with the newsletter.

With all the dating apps available that encourage instant gratification, do you think they make it harder for people to find partners that could lead to long-term relationships?

HO: I do. I think it’s certainly possible. I’ve met amazing people through dating apps, and I have friends who are very happy in long-term relationships with people they met on Tinder and Hinge. The problem with dating apps is that it feels like a game.

You know, it’s more exciting to swipe and make matches than it is to actually go out on these dates. People get pretty caught up in that aspect of it, and forget that these are real human beings in front of them, and it’s not just characters or avatars. That’s not to say that dating apps are bad, but I don’t think they’re the most efficient or most effective way to find a relationship if that’s what you’re looking for. 

How do you match people?

HO: The newsletter is a twist on the classic matchmaking concept. When I worked professionally as a matchmaker, I’d work one-on-one with clients. It was a really in-depth process of really getting to know my clients, their lifestyles, what they’re looking for, their values, and I’d cast a wide search net and do that same process of getting to know people in order to find the matches. 

At this service, it was $600 a month per client for two dates a month, but this matchmaking newsletter is totally free. Because of this, my process is a little bit different. 

What I do is I profile amazing New Yorkers that I think more people should know about; singles looking for dates, for relationships, and then from there, if the person is interested, they can reach out to me like, “I think so and so is really amazing can you put me in touch?” and that’s what I do 一 a more personalized introduction. 

Do you meet singles in person before the dates?

HO: It depends. Some of the people I do know personally, others I just communicate with via email. It’s a thorough process. I make sure they’re not strangers. I really want to make sure that these are people that I feel comfortable personally vouching for. 

How do you attract new clients? Do you attend networking events to promote your newsletter?

HO: It’s really through social media and word of mouth. I’ve been lucky that word spreads pretty quickly that way.

What do you think are the best places to meet new people?


HO: That’s such a good question! A lot of my favorite places to meet new people is going out with friends, especially if your friends are really social and friends who throw amazing parties. I’m always meeting their friends or their boyfriend’s co-workers, etc. When you’re with your friends, the pressure is off, and they can vouch for them. I personally have had a lot of success that way, but you can meet people everywhere. 

I met my last boyfriend at this Jewish singles dance held on Christmas Eve every year called the Matzo Ball dance. My parents met there on the exact same night Christmas Eve 1987. You can meet people anywhere. It doesn’t have to be through a dating app. You can meet people on the subway. 

When I was a matchmaker with Tawkify, I used to hit on people on the subway and say, “This is not for me, this is for a client.” It was just a matter of going up to them and saying, “You’re reading a really interesting book, can we talk?” and I would give them my business card. 

Which places do you recommend for a first date?

HO: The drinks date is a classic, and everyone in New York does it. It’s quick, it’s easy, but I prefer something that’s more creative like walking through Central Park or visiting a museum. 

There are so many amazing things to see here, and it’s really special and fun if you can introduce your date to something that you really enjoy. I think something that’s really fun on a first date is that if you want to go the drinks route, which is safe and easy, pick a bar that has a pool table or there's jazz playing. 


If it’s in the fall, a haunted house would be a really fun first date. If your friend is doing a comedy show or an improv show, bring your date along. That’s really fun and that way you can show your sense of humor, your circle, and your scene.  

You’re about to be a published author. Can you please tell me about your book?


HO: The book is called Playing with Matches and it comes out in 2018. My publisher is Touchstone Books (an imprint of Simon & Schuster). Playing with Matches is inspired by my real-life experiences as a matchmaker. 

It’s about a 22-year-old girl who graduates from college and doesn’t get the job she expects to get. She scrambles to find a new job and ends up working as a matchmaker for an elite dating service based in New York City, her personal life and her professional life collide, and things get complicated. 

You’ll have to read it to find out what comes next!

Subscribe to "Playing with Matches" to see singles or sign up to be matched by Hannah. You can and should also follow Hannah on Twitter

[via Elyssa Goodman] 

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