
How To Date Intentionally This Cuffing Season
Cuffing season is here, but why does everyone suddenly want to couple up when the weather turns cold? In this episode, we dive into the psychology, cultural pressures, and real dating app data behind ...
25 Sep 202539min

Why Some Couples Divorce and Others Find Their Way Back
Divorce lawyer Jonathan Merel joins the podcast to share what he’s learned about love, marriage, and relationships from his years in family law. We talk about why couples file for divorce, how often p...
23 Sep 202540min

Our New Home & Our Unpopular Take on Wedding Speeches
Jake and I are officially in our new apartment (!!) and we’re unpacking all the highs and lows of moving week — including Ilana’s unexpected side gig babysitting our TaskRabbit’s kid. We also get into...
22 Sep 202545min

From Finance Bro to Full-Time Musician: Owning Your Story in Dating
I’m joined by musician Brett Altman, who recently left his finance career of 9 years to finally pursue music full-time and discovered that owning your story can completely change the way you date. We ...
18 Sep 202546min

What Happens When You Sit Down With All Your Exes
Miriam Katz just launched one of the boldest projects in the dating world: a podcast where she interviews every single person she’s ever dated. They talk about what it’s really like to sit down with e...
16 Sep 202547min

Should You Reach Back Out or Let Them Go?
It’s our final episode in this apartment before the big move, and Ilana’s type A side is showing in full force during the packing process. In between boxes, we answer your questions about dating and r...
15 Sep 202542min

Answering Your Biggest Dating & Friendship Dilemmas
In this solo Q&A, I’m answering your biggest dating and friendship dilemmas — from why your ex still watches your Instagram stories, to how to say no to being a bridesmaid, to figuring out if “I’m not...
11 Sep 202549min

Dating Burnout, Rock Bottom, and the Power of Being Alone
After years of back-to-back heartbreaks, author Abby Rosmarin hit relationship rock bottom and made a radical decision: she stopped dating—completely—and committed to an entire year of choosing hersel...
9 Sep 202549min


















