I attended a coaching session with an elite matchmaker after the relationship ended


I attended a coaching session with an elite matchmaker after the relationship ended

  • New York City-based matchmaker Rori Sassoon offers one-on-one coaching sessions for $500.
  • During my hour-long session with her, we discussed my past relationships and my current dating goals.
  • I didn’t feel judged for keeping my dating life easy and staying off dating apps.

When Rori Sassoon, co-founder of dating service Platinum Poire in New York City, offered me an hour of personal dating advice and coaching, I thought: Why not?

Sassoon has been a matchmaker for nearly two decades, and her business caters to people in their 30s, 40s and 50s who can afford a $15,000 six-month membership. Sassoon said she wanted to extend her work to millennials and non-members as well, so she launched her coaching service on May 1st. For $500, a client gets one hour of Sassoon’s time to discuss their dating history, current experience, and ultimate goals on how to achieve them, either in person or via



After my Zoom session — in which Sassoon supported my decision to stay off dating apps and hailed my looks, personal and professional accomplishments, and outspoken demeanor — I felt stronger, on my own terms, and with a little more patience on the to stay current.

First, the matchmaker asked about my dating history

Before my session, I completed a short questionnaire about my past relationships and dating goals.

Sassoon said she has worked with clients who have never been in serious relationships and others who have been married for 20 years. So, the intake form helps her open up those conversations and offer tailored advice.

At the beginning, Sassoon asked me if I would rate my previous relationship, which lasted almost 10 years and ended 9 months ago, as one of the best romantic ones of my life. I said yes. We talked about how we had lived together, what qualities I liked in my ex, and how I wish our relationship could have been different.

It wasn’t comfortable warming up to the best relationship of my life, and I worried about feeling judged for having little remorse or criticism about the dynamic between my ex and I.

But talking to Sassoon made me feel empowered. Discussing my past felt like a research project to improve the quality of my current dating life.

She supported my decision to stay off dating apps and have casual sex

I expected Sassoon to say that my current approach to dating—lots of first dates, casual affairs, and sex when I feel like it—was dead wrong.

But Sassoon only asked follow-up questions to better understand my mentality and the people I would date. She ended up offering me two pieces of advice on casual dating that I want to keep in mind.

1. Don’t compromise on your relationship values.

I told Sassoon that I have trouble finding partners I’m attracted to, both socially and sexually, who want to continue seeing me. After spooking two matches in two months, I began to wonder if I was asking too much.

But Sassoon said I would benefit more in the long run by sticking to my relationship values.

Now, when I notice signs that a match isn’t respecting my time or not being transparent about their feelings, I try to take a moment to be sad about that lost connection without assuming that I did something wrong.

2. Be open, not obsessed with finding connections.

I also told Sassoon that I’m hesitant to use dating apps again after deleting them from my phone a month earlier. At the same time, I worried that I wouldn’t otherwise have the opportunity to meet new people.

Sassoon, whose entire business is helping people leave apps to make real-life connections, said not to worry.

Instead, she suggested that I change my mindset and focus on flowing into myself. She told me to take the time and energy I used to spend on dating apps and instead interact with the real world, whether it’s having dinner with friends, running errands, traveling, or doing anything else that I am in love.

In Sassoon’s experience, people tend to behave in a positive and fun way, and it’s easier to embody this when you’re enjoying life and have confidence that you’ll meet great people. She told me to draw the line between “hunting” for a match and sealing my connection.

It felt like I was talking to a supportive and non-judgmental older sister

I left my session with Sassoon feeling grounded and confident. She was like a confidante and conspirator, and it was refreshing to have an upbeat yet realistic conversation, especially after a few months of weariness over my prospects.

Still, I couldn’t help but think that the $500 fee would be better spent on a handful of therapy sessions.

I thought of myself when I first started therapy a year ago and all the stories I had internalized about myself that I needed to unlearn.

I am more confident in myself as a friend, sister, daughter and lover because I have done this work. Without therapy, I don’t think my session with Sassoon would have had the same meaning.

Of course, I take encouragement wherever I can get it because dating is hard work. But I would be remiss if I didn’t also acknowledge the immense personal work that goes into dating.

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