Today, we’re visited by one of our favorite. Ilana Dunn Solomon—dating coach, content creator, and the voice behind Seeing Other People, a podcast that’s basically the internet’s wisest, funniest older sister. Ilana’s known for cutting through the noise of modern dating with raw honesty, zero judgment, and the kind of insights that make you feel both called out and comforted.

But today, she’s not here alone. She brought backup—her husband, Jake Solomon.
The man who went from first date to fiancé to full-on husband in a love story that has unfolded both publicly and privately, with all the chaos, clarity, and chemistry that comes with it.

In this episode, we’re diving into all of the hilarious, and deeply human moments that makes a marriage. We’re talking about the difference between butterflies and real compatibility, and the myths people still believe about love.
We’re also talking dating app burnout, emotional availability, male perspectives, green flags, and everything that comes up when a dating expert marries someone who perhaps never expected to be part of the discourse...

Episode Breakdown:

00:00 - Intro: Welcome Alana & Jake
00:36 - How They Met: A Hinge Love Story
02:02 - The Early Stages of Dating
03:26 - First Impressions on Their First Date
05:05 - COVID Dating & Timing
06:22 - Was Dating a Dating Coach Intimidating?
07:42 - Launching Seeing Other People
08:24 - The Engagement Story
10:49 - When She Knew He Was "The One"
12:26 - Married Life & Moving In Together
13:38 - Living Together Adjustments
15:08 - The Great Sock Debate
16:32 - Family Dynamics & Holidays
18:57 - Marriage Myths That Aren’t True
20:09 - Dating Your Partner After Marriage
21:04 - Their Best & Worst Dates
24:43 - Newlywed Game: He Said / She Said
31:24 - Dating Advice Men & Women Need to Hear
32:59 - The Dating App Feature They Wish Existed
34:39 - Are Nice Guys Out?
36:16 - Why Aren’t More Men at Singles Events?
39:09 - The Fear of Rejection in Dating
40:23 - Are We Obsessed With Being Chosen?
43:30 - Advice for Burned-Out Daters
45:26 - Managing Dating Expectations
47:01 - Their Own First Dates Reflection
48:09 - How Well Do You Know Each Other? Quiz
50:27 - Closing & Final Thoughts

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