If you want to know what’s really in New Yorkers’ hearts, just ask a matchmaker.
When she was just 21, Hannah Orenstein worked for the matchmaking service Tawkify and learned all too well what men are looking for in a mate.
“So many … wanted a woman who looked like Scarlett Johansson that I just started abbreviating her name to initials in my notes,” says Orenstein, now 25 and an Upper East Side resident. If that didn’t seem like a stringent enough requirement, she had one man who wanted “Scarlett Johansson’s face with a yoga instructor’s body.”
The seven months Orenstein spent on the job inspired her new novel, “Playing With Matches,” a comedic look at the life of a young matchmaker struggling to balance her personal life with her profession.
“I met amazing men every day, which was encouraging,” says Orenstein. “But I also met more than my fair share of men who didn’t seem to respect women fully, and that was disheartening. I had trouble dating while working as a matchmaker and for months after.”
When she worked at Tawkify, the company’s approximately 240 clients paid the service $600 a month to find them a perfect match. Orenstein received $120 for each date she arranged, despite the fact that the only relevant experience she had was setting up fellow students for a campus blog while at New York University.
“The only understanding I had of matchmaking came from the ‘Millionaire Matchmaker,’” she says.
Tawkify’s glam clients — the service helped pair burlesque dancer Dita Von Teese with a Scandinavian novelist — tended to be quite picky. The general rule was to try to set up people who were equally attractive and equally successful. But, for some, that wasn’t enough.
One finance bro was looking for a woman who was “tall, breast-y, 5-foot-7 or above, implants preferred,” she says. Also on his list of requirements: “She should make a good salary unless she works in fashion or is a model, in which case he wouldn’t mind supporting her.”
Orenstein chose not to work with him.
Then, there was the 40-something Bollywood star. He was charming and extroverted, but Orenstein noticed that he was flanked in most of his pictures by very young women. When she asked him about his preferred age range he replied, “There are some very mature 18-year-olds.”
‘I met more than my fair share of men who didn’t seem to respect women fully, and that was disheartening.’
He wasn’t the only one looking for young women. Orenstein would use her own name and age when looking for eligible candidates on dating apps, which, along with family connections, LinkedIn and recruiting eligible people on the subway, were her main means of finding people. (Most of her colleagues also relied on dating apps, although the services don’t like having matchmakers on them, and Orenstein says she was constantly being kicked off some of them.)
The young matchmaker used as many as eight different apps. She’d initiate a conversation with a man, then tell him she was actually looking to set them up with a client. No one was ever outraged over the bait-and-switch. However, Orenstein says, many people asked, “Are you sure I can’t date you?”
Such questions from older men made her feel that, “by 21, my time was already running out.”
Guys weren’t the only ones with outrageous criteria. Orenstein recalls one woman that came in with a detailed checklist. When she set her up with an eligible man she rejected him for having “obese knuckles.”
“He had a very average frame!” Orenstein says. “His knuckles seemed fine-looking to me.”
However, she claims that in general, “Men were more picky about looks, women were pickier about chemistry.”
Orenstein’s matchmaking career eventually came to an end. The long hours and nature of the work got to her.
“Even though I loved my job, I found it pretty emotionally exhausting,” says Orenstein, who took an internship at Cosmopolitan soon after. “I couldn’t summon the energy required to form an authentic connection on dates for months afterward.”
That’s not a problem now. For the past eight months, Orenstein has been happily dating a 26-year-old software engineer she first met on Tinder and then reconnected with on Hinge. She’s still in the romance industry, working as the dating editor for the Web site Elite Daily, but she no longer sets people up, even friends.
For those who are interested in occasionally playing matchmaker for buddies, Orenstein suggests proceeding with caution.
“If you can’t think of three really good reasons these people would get along, shy away from [it],” she says. “If you’re just saying, ‘Oh, you’re both Jewish!’ that’s not a good enough basis for a match.”
What not to do on a first date
Be rude to the waiter
If you can’t treat other people with kindness and respect, that’s a huge red flag, says dating expert and former professional matchmaker Hannah Orenstein.
It makes a terrible first impression, and can give the idea that you think your time is more valuable than theirs, says Orenstein.
Dominate the conversation
Ask your date questions, she says. Otherwise, what’s the point of dating?
Be outwardly nervous
If you appear to be at ease your date will be, too, says Orenstein. Confidence is hot!
Order for your date
It’s so old-fashioned, presumptive and rude, she says.
Bring up your ex
You have just one chance to make an amazing first impression, Orenstein says. Why waste time dwelling on the past?
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