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Just The Tips: Meet Playboy’s New Advice Columnist

Just The Tips: Meet Playboy’s New Advice Columnist: Eileen Meny

Eileen Meny

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Katherine Cooper’s business card says “matchmaker,” but she prefers to tell people she’s a “consultant.” A “dating consultant,” she explains over a glass of rosé on her Brooklyn rooftop. “It makes me feel less like I’m playing god.”

Traditional matchmaking still exists—just blocks from where we’re sitting, matchmakers are literally doing God’s work in the Hasidic parts of Crown Heights—but Cooper’s domain is mostly confined to the Tinderverse and Park Slope, as opposed to all of earth and heaven. Her clients pay her company Tawkify $599 per month for the privileges of personalized dating attention and one guaranteed monthly date. Filling out a profile means noting dealbreakers as well as your date’s expected income. Her clients are people who are extremely busy with their careers, and in search of high-achieving partners—or maybe stay-at-home ones—who can keep up.

“A lot of what clients are paying us for is to navigate some of the very uncomfortable waters of dating,” Katherine explains. “Sometimes that means me meeting a bunch of people through whatever means possible. Sometimes it means having bad conversations to weed out people that are not worth others’ time.” Essentially, she’s distilling the mess of noise that online dating has become for a client who doesn’t want to deal. Setting up matches for more than 50 couples in the past year, she’s become an accidental expert in online dating along the way.

Next week, she’ll begin sharing her wisdom in a weekly advice column called Just The Tips: Dating Etiquette in a Digital Age. Today, we wanted to give readers the chance to know the columnist a bit better. Playboy caught up with Katherine this summer to discuss life as a matchmaker and online dating pitfalls.

PLAYBOY: So what makes you qualified to be a matchmaker?

COOPER: Well, I fall in love very easily, so that’s number one. But also, I have a fundamental belief that everyone deserves love. And that it’s possible for everyone to find someone. Not everybody believes that.

PLAYBOY: And how is that playing out in practice? You’ve made matches?

COOPER: Yeah, I have. I haven’t been doing it for long enough to have any marriages, although two of Tawkify’s clients—former clients—just eloped. Big deal!

PLAYBOY: Congrats. So, how does it work? How do people find you?

COOPER: You’re alone in your apartment, and you’re like, I’d really like to go on a date, and if I get sent one more dick pic or have to read one more novel about somebody on OkCupid, I’m going to hang myself in the bathroom. So then you would find us—most likely through word of mouth but possibly because you knew of the illustrious E. Jean Carroll (Elle columnist and former Playboy contributing editor) or Kenneth Shaw (a tech entrepreneur), our two founders.

PLAYBOY: Is that how your company is positioning itself—as absorbing the shittiness of online dating on behalf of the client?

COOPER: People want to go out and meet new people—but not any scary ones. Part of what a matchmaker can do is help ease that transition into broadening the edges of whatever your given community is.

PLAYBOY: If I were a new client, what would happen?

COOPER: First, I would read your profile carefully. Then we’d meet up at a place that was convenient for you. We would sit down for an hour, and I would listen to you. Really carefully.

PLAYBOY: And you would ask me to talk about my dating history?

COOPER: Not necessarily. Dating history is relevant, but I like to talk to people about how they grew up, actually, and whole life stories. Of course, we run into relationships along the way. But if I just told you about the people that I’ve been in love with, I think you’d have a weird idea of who I was.

PLAYBOY: So then what’s step two.

COOPER: Step two: I start cruising. Sometimes that means giving my card to somebody that I meet at a party. Sometimes that means emailing a professor of microbiology at Columbia. Sometimes it means going to some of those other online dating venues. It’s a lot of conversations—sometimes bad ones. I’m a 28-year-old woman, and I look through my eyes. In a way, it’s curating for the clients. Curating with care. The world is full of options.

PLAYBOY: You’re essentially going on first dates for other people. Is part of the job using your own sex sex appeal?

COOPER: I think that people are craving intimacy, and I feel like I am trafficking not in sex appeal, but in my own empathy and intimacy. I meet with people for a set period of time and they have my presence, and they can tell me whatever they want. In my mind, I’ve likened it to therapy.

PLAYBOY: Which means you probably give great advice. What will you talk about in Just the Tips?

COOPER: Candid advice on the manners, mores and ethics of sex, love and dating. Sometimes philosophical, occasionally funny, always heartfelt, and above all, real. There are no rules in love and war but there might be some guidelines.

PLAYBOY: How has your experience as a match-maker shaped the way you advise people about their dating lives?

COOPER: Well, honestly it’s made me more empathetic and less patient. Each person we meet is going through it in one way or another. Universally, humans need to be loved and seen. Most of us need to have sex too. I advise people with the knowledge that we are all valiant, strong, sensitive people who are also very needy.

PLAYBOY: What kind of missteps are common in online dating?

COOPER: High expectations. Low confidence. The misconception that the internet can provide us with an infinite stream of new people. A waning appreciation for the arts of flirtation, seduction and romance and a lack of appreciation for delayed gratification.

The biggest misstep people make is to forget that we have control over how we interact with the online world. It’s up to us to makes sure we exit a date or a text message exchange without feeling like a terrible person. The internet and its false promise of anonymity will invite us to do otherwise but it’s entirely within our control to behave gallantly online.

PLAYBOY: What is it like being in a business where if you’re successful and make a match it means the client won’t return?

COOPER: Sad, but you know. It’s like childbirth—you make something, and then you let it go.

PLAYBOY: They’ll be back?

COOPER: They might be.

Have a question for Katherine about sex, love or dating? Shoot her a note at justthetips@playboy.com.


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