🎙 The most awkward first kiss with Ilana Dunn & hubby Jake 💋

04/04/25 • 40 min

In this episode, I sit down with Ilana and Jake to chat about their relationship journey—how they met, what keeps their connection strong, and the little things that make love last.

We dive into:

💘 Their Hinge love story and first date moments

🎟️ The creative ‘date card’ activities and spontaneous trips that keep things exciting

😂 A hilariously awkward first kiss story (and how Elana made theirs unforgettable)

🗣️ The power of communication, fun, and support in a relationship

🎙️ Ilana’s insights as a podcast host and dating coach on vulnerability and authenticity in dating

This episode is full of laughs, love, and real talk about what makes relationships truly work.

🔔 Tune in and get inspired to bring more fun and connection into your own love life!

Support the show

Contact Aleeza Ben Shalom https://marriagemindedmentor.com/
Contact Rabbi Yisroel Bernath https://www.theloverabbi.com/
Submit a Question for the Matchmaker, Matchmaker Podcast https://marriagemindedmentor.com/podcast/

In this episode, I sit down with Ilana and Jake to chat about their relationship journey—how they met, what keeps their connection strong, and the little things that make love last.

We dive into:

💘 Their Hinge love story and first date moments

🎟️ The creative ‘date card’ activities and spontaneous trips that keep things exciting

😂 A hilariously awkward first kiss story (and how Elana made theirs unforgettable)

🗣️ The power of communication, fun, and support in a relationship

🎙️ Ilana’s insights as a podcast host and dating coach on vulnerability and authenticity in dating

This episode is full of laughs, love, and real talk about what makes relationships truly work.

🔔 Tune in and get inspired to bring more fun and connection into your own love life!

Support the show

Previous Episode

Juicy Dating Stories from a TikTok Celeb

In this episode, I sit down with Chloe Hechter, a Jewish influencer whose hilarious TikTok content has taken the internet by storm. But behind the viral videos, Chloe shares what it’s really like to date as a public figure—from painfully awkward first dates to the challenge of finding someone who sees past her online persona.

Here’s what we dive into:

✔️ The worst first date of Chloe’s life (trust me, you’ll cringe!)

✔️ My Five Date Challenge—can it help her find real connection?

✔️ Why dating as a Jewish influencer in NYC is way more complicated than you’d think

✔️ The search for a deep, intellectual partner who’s more into books than TikTok

If you’ve ever struggled with dating in a digital world—or just want some juicy dating stories—you need to hear this one.

Support the show

Next Episode

🎙 Finding Love in the Social Media Age with Libby Amber Shayo

🎙 Finding Love in the Social Media Age with Libby Amber Shayo
In this episode I’m joined by newlywed Libby Amber Shayo, who shares her love story—how she met her husband through her social media presence and her now brother-in-law.
We chat about:
❤️ Tips for dating influencers
📱 How she balances social media and her relationship, OY!
⏸️ Why taking breaks from dating can actually help
Whether you wanna date an influencer or are just curious about love in the digital age, this episode is for you.
🔔 Tune in now—I can’t wait for you to hear this one!

Support the show