I visited an elite $500 an hour matchmaker after my 10 year relationship ended. She said 2 things that gave me confidence to date casually.

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

When Rori Sassoon, co-founder of New York City matchmaking service Platinum Pear, offered me an hour of one-on-one 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 subscription for six months. Sassoon said she wanted to expand her work to also include millennials and non-members. So she launched her coaching service on May 1. how to reach them, either in person or more



After my Zoom session — where Sassoon supported my choice to stay off dating apps and showcased my looks, my personal and professional successes, and my outspoken attitude — I’ve felt more empowered to date on my own terms. and with a little more patience.

First, the matchmaker asked me about my dating history

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

Sassoon said she had worked with clients who had never been in serious relationships and others who had been married for 20 years. The intake form therefore helps her to open these conversations and offer personalized advice.

To start, Sassoon asked me if I would characterize my previous relationship, which lasted almost 10 years and ended 9 months ago, as one of the best romantics of my life. I said yes. We talked about how we had lived together, the qualities I liked in my ex, and how I wish our relationship had been different.

It was not pleasant to dwell on the best relationship of my life, and I was afraid of feeling judged for having few regrets or criticisms of the dynamic that my ex and I had.

But talking to Sassoon, I felt stronger. Discussing my past felt like a research project to improve the quality of my current love life.

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

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

But Sassoon only asked follow-up questions to better understand my mentality and the people I was dating. In the end, she offered me two casual dating tips that I plan to keep in mind.

1. Don’t compromise on your relationship values.

I told Sassoon that I had trouble finding partners who were both socially and sexually attractive to me and who wanted to keep seeing me. After two games slipped away from me in the space of two months, I started to wonder if I had asked too much.

But Sassoon said I’d get more out of it in the long run if I stuck to the values ​​of my relationship.

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 feel sad about that lost connection without assuming I’ve done something bad.

2. Be open and not obsessed with finding connections.

I also told Sassoon that I was hesitant to use dating apps again, after deleting them from my phone a month ago. At the same time, I feared that I would not have the opportunity to meet new people if I did.

Sassoon, whose entire business is helping people leave apps to connect in real life, said I shouldn’t worry.

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

In Sassoon’s experience, people gravitate towards positive, fun demeanor, and it’s easier to embody that when you’re enjoying life and confident you’ll meet great people. She said to draw the line between “chasing” a match and closing me on the connection.

I felt like I was talking to an older sister who supported me and didn’t judge me.

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

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

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

I’m more confident as a friend, sister, daughter, and lover because I’ve done this job. Without therapy, I don’t think my hour with Sassoon would have had the same gravity.

Of course, I will take encouragement wherever I can find it, because dating is hard work. But I would be remiss if I did not recognize the immense personal work involved in meetings.

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