Sometimes Cupid eats bagels, speaks fluent French and takes the subway.
Hannah Orenstein, 21, finds love matches for her clients at coffee shops, bookstores, concerts and dinner parties. The New York University journalism and history senior never planned to become the Big Apple’s own Cupid, but her experience as a dating writer and her interest in all things love and romance made the career a perfect match when an opportunity to join Tawkify, a San Francisco and New York-based matchmaking startup co-founded by E. Jean Carroll and Kenneth Shaw, presented itself. And Orenstein loves her work.
“It’s wonderful to be in a job where I’m really making a difference in someone’s life,” Orenstein says. “We all want to love and be loved, and that I get to help someone experience that is incredibly powerful and something that I really treasure.” When she isn’t setting up dates for her high-profile clients or searching for their perfect matches, she writes articles for NYU Local, Bustle, xo Jane, Thought Catalog and Jewcy and manages editorial for the HBIC Project, which highlights the accomplishments of twenty-something women.
We talked with Hannah Orenstein to find out what it takes to be a professional matchmaker.
Feather Magazine: How did you get started as a matchmaker?
Hannah Orenstein: I grew up in Boston and read a column called “Dinner With Cupid” that the Boston Globe Magazine publishes every week. The magazine would put two people on a blind date then interview them afterward and write about their experience. So when I started writing for NYU Local, which is the student blog at NYU, I pitched a similar column to my editor, and it was a really fun and successful column. I did that for about a year. Then, last fall, I interned at Elle Magazine and worked on a project that impressed advice columnist E. Jean Carroll so much that she complimented me, and we stayed in touch. I went to Paris for spring and began looking for a summer job. Carroll’s matchmaking service Tawkify had never hired a college student before, and I asked if I could be the first. I’ve been here ever since.
FM: What is a typical workday for you like?
HO: Tawkify’s office is in San Francisco, so the matchmakers in New York work from home. I’m really lucky because I get to make my own schedule. So I get up and go through my emails. If I had a client go on a date last night, I will follow up with them immediately and see how it went. I call both people and ask them if they enjoyed the date or had anything to tell me and get their perspectives on the date. Then I spend another portion of the day scouting matches for my clients. If I have a new client, I’ll meet with them the first time for coffee or cocktails and talk for an hour or two about their life, their dating history and what they’re looking for in a relationship. Another part of my day is interviewing and screening potential matches for my clients. Then I am coordinating schedules and planning creative dates. My schedule is flexible because it depends on how many clients I have and what I need to do that day.
FM: How do you find matches for your clients?
HO: My job as a matchmaker means that I work with my clients to identify their dating needs and specifically searching for potential matches. We find matches from all over. While we do have a database, I’m not limited to that. The city is our dating pool. So it could be someone from the database, or it could be someone in my own network.
FM: What makes a good match?
HO: One thing people overlook [when looking for romance] is the importance of compatible lifestyles. For example, I would match someone who has children with someone else who has children because they would understand that lifestyle. Basic lifestyle compatibility tells a lot about a match and can predict success as well. It’s also important to look at personality more than common interests. The success of a relationship is not going to be built on a common interest, though that’s nice; it’s going to be based on how they are together and on mutual respect, love and compatibility.
FM: What qualities or skills does a person need to be a good matchmaker?
HO: Every matchmaker needs to be a really good listener. You have to listen to your clients’ and where they’re coming from. You also need to have a little intuition because maybe they’re saying one thing but they might actually be happier with another thing. Some insight into psychology is really helpful. Overall, it’s best to have great communication skills because you need to be on top of your emails, phone calls and texts. Writing skills are also important. Being creative makes a difference because we don’t like to do boring dates. There’s nothing that kills romance faster than being in a fancy restaurant and sitting across your date with so much pressure on you. It’s nerve-wracking and not fun. So the more creative you can be, the better. We send them out on dates for all kinds of things, like safaris or something else adventurous.
FM: What advice do you have for someone who wants to start their career as a professional matchmaker?
HO: Do it as a hobby and build up success stories. You can join an established matchmaking service like Tawkify, but there’s really no one career path or one way to break into the industry. But it’s key to have passion for what you do and commitment to make it happen.
“So You Want To Be…” is a feature that highlights women with awesome jobs. If you know someone we can interview, email Life Director Alyssa Ammirato, at alyssa [at] feather-mag [dot] com.