Stranger Sessions: The Jewish Singles Version

I came across one of the most unexpected matchmaking experiments I've ever seen.

Meet Paisley Drouin, a 20-year-old photographer from Prince Edward Island who is creating "Stranger Sessions" – bringing together two strangers for the first time and photographing them as if they're already a couple.

No awkward small talk or uncomfortable first dates. The participants are asked to step into the energy of two people who have been together for a while, comfortable, connected, playful. Maybe even a little bit in love.

I was blown away by Paisley’s photos. Chemistry isn't something you can manufacture with a camera. This couple truly looked like a match.

For her first Stranger Session, applicants filled out a questionnaire that Paisley carefully reviewed, and then she selected a pair she thought would fit well together.

"All of the questions they answered were the same,” Paisley explained to me. “Hobbies, interests, music taste. They both like the country, they love working out, they both have great jobs and were both really looking for something serious. The only thing they answered differently was how social they were. She answered more introverted and he answered more outgoing. I thought they would be the perfect pair!"

The photos were breathtaking. There was ease, warmth, and curiosity. During the photo shoot they weren't yet a couple. But after the shoot they continued talking, then they went on a few dates and get this: Paisley's intuition proved correct. They just made it official. They are now a couple.

Now one successful match doesn't prove a system. So Paisley tried it again. This time she was half right. One participant was interested, the other wasn't. I think that’s still a great outcome. In matchmaking, success isn't measured by whether every introduction leads to marriage. Success is creating opportunities for two people to discover whether there is something worth exploring.

Sometimes one person sees potential while the other doesn't. That's dating. What fascinates me about Stranger Sessions is the psychology. When people show up on a traditional first date, they often arrive carrying fear, pressure, and expectations. Do they like me? What should I say? What if I say the wrong thing? What if they reject me?

But when someone steps into a stranger session photoshoot, they're being asked to imagine a connection instead of evaluating it. They're focused on presence instead of performance. And something interesting happens when two people stop interviewing each other and start experiencing each other.

That doesn't guarantee compatibility but it does create space for curiosity. One of my favorite pieces of dating advice is simple: Don't ask, "Is this my soulmate?" Ask, "Am I curious to learn more?" Curiosity creates possibility, and possibility creates opportunity.

I was so excited by Strangers Sessions, I reached out to Paisley to collaborate with her! On July 9th, we'll be in New York City creating two Stranger Sessions exclusively for Jewish singles.

But there's a twist. I presented Paisley with a challenge: no touching. My goal is for them to touch hearts before other parts. As someone who teaches singles to build emotional intimacy before physical intimacy, I wanted to see whether we could capture connection without relying on physical contact. Can two people communicate interest through eye contact? Can curiosity be photographed? Can warmth, chemistry, and possibility be captured without anyone holding hands, hugging, or leaning on each other?

I think the answer is yes and I'm excited to find out.

So if you're a Jewish single in the NYC area—or willing to travel there on July 9th—consider this your invitation. Apply. Take the leap. Trust the process.

You'll receive absolutely no information about the other person beforehand. No profile, no photo, no bio, no social media stalking. You simply show up, meet your fellow stranger, and step into the experience.

Will it lead to a relationship? Maybe. Will it create a memorable story? Definitely.

We'll be documenting the experience and sharing the results afterward. So whether you're applying or simply cheering from the sidelines, stay tuned and check back soon for the follow-up article.

May we be blessed to make a match and may you be blessed to make a match too!

Apply for the NYC Stranger Session and I’ll meet you in NYC!

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