I Met My Match: Why Successful Women Stay Single (with Netflix’s Aleeza Ben Shalom)

Remember how I told you I got engaged in just two weeks? Well, this week, I met my match. Literally.

I recently sat down with the one and only Aleeza Ben Shalom—yes, THE Jewish Matchmaker from Netflix. She is the real deal. And here is the wildest part: her own love story is almost identical to mine. You absolutely have to hear it.

We went there, and we didn’t hold back.

The #1 Thing Holding Successful Women Back

As someone who has matched thousands of Jewish couples, Aleeza knows exactly what works and what doesn’t. So, I had to ask her the one question I get asked more than anything else when I travel and speak:

Why are so many brilliant, successful, stunning women—women who have built whole, beautiful lives—still walking away from the right person?

Her answer genuinely surprised me, and I think it will surprise you too.

Inside the Episode: Dating Rules, Mistakes, and “HQs”

We dive deep into the modern dating landscape, covering:

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• The dating rule almost nobody wants to hear: The one she swears works every single time (and bonus: the men actually love it).
• The single biggest mistake: The recurring pitfall she sees brilliant women make over and over again.
• The “HQ” (High-Quality Human): The guy who might not be the loudest or hottest in the room, but is exactly the one you should never stop dating.

Red Flag, Green Flag 🚩 🟩

Oh, and then things got really fun. We played a brand-new round of Red Flag, Green Flag, debating scenarios like:

• He doesn’t pay on the first date.
• He is not a great texter.
• He wants to be a stay-at-home dad.
• He is a little too close to his mother.

Let’s just say, Aleeza and I did not always see eye-to-eye on these!

Watch the Full Episode Now

Pour yourself a coffee, get cozy, and come sit with us.

👉 Click here to watch the full episode on YouTube!

Over to You!

The second you finish watching, come back here and tell me in the comments below which of those scenarios you would call a red flag. I have a feeling you are going to have some strong opinions, and you know there is nothing I love more than hearing from you.

See you next Wednesday with a brand-new episode!