• 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 previous relationships and current dating goals.
• I didn’t feel judged for keeping my dating life casual and staying off dating apps.

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

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

Zoom

.

After my Zoom session — where Sassoon supported my choice to stay off dating apps, and hyped up my looks, personal and professional successes, and candid demeanor — I felt more empowered to date on my own terms and with a bit more patience.

First, the matchmaker asked about my dating history

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

Sassoon said she’s worked with clients who’ve never been in serious relationships, and others who’ve been married for 20 years, so the intake form helps her open those conversations and offer tailored advice.

To start, Sassoon asked me if I would characterize my previous relationship, which was almost 10 years long 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, the qualities I liked about my ex, and the ways I wished our relationship could’ve been different.

It wasn’t pleasant rehashing the best relationship of my life, and I worried about feeling judged for having barely any regrets or critiques about the dynamic my ex and I had.

But talking to Sassoon, I felt empowered. Discussing my past felt like a research project for improving 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 my current approach to dating — lots of of first dates, casual flings, and sex when I feel like it — was all wrong.

But Sassoon only asked follow-up questions to better understand my mentality and the people I’d mesh with on dates. In the end, she offered me two pieces of casual dating advice I plan to keep in mind.

1. Don’t compromise on your relationship values.

I told Sassoon I had trouble finding matches who I felt both socially and sexually attracted to, and who wanted to continue seeing me. After two matches ghosted me within a two-month span, I started to wonder if I’d been asking for too much.

But Sassoon said I’d benefit more in the long run if I stuck to my relationship values.

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

2. Be open to, not obsessed with, finding connections.

I also told Sassoon I was hesitant to use dating apps again, after deleting them from my phone a month prior. At the same time, I worried I wouldn’t have any opportunities to meet new people if I did.

Sassoon, whose entire business involves helping people get off apps to make connections in real life, said I shouldn’t be concerned.

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

In Sassoon’s experience, people gravitate towards a positive and fun demeanor, and it’s easier to embody that when you’re enjoying life and trusting you’ll meet great people. She said to tow the line between “hunting” for a match and closing myself off to connection.

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

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

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

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

I’m more sure of myself as a friend, sister, daughter, and lover because I did that work. Without therapy, I don’t think my hour with Sassoon would’ve held the same gravity.

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