Red Flags or Dealbreakers? What We'd Think Now vs. When We Were Single
Happy Monday! We're recording from Jake's childhood bedroom fresh off a wedding the night before. We talk about why we're obsessed with vows and speeches, what it's like to hear other couples' love st...
8 Jun 49min
My Dating Mistakes I Understand Differently Now
This solo episode is all about hindsight, growth, and the dating choices I understand differently now. I’m reacting to listener-submitted scenarios through two lenses: what past me probably would’ve d...
4 Jun 47min
Fertility Anxiety, Egg Freezing & Dating Under Pressure
Lauren Makler joins the podcast for a conversation about fertility anxiety, egg freezing, dating pressure, and the emotional weight so many women carry around timelines. From AMH testing and IVF to se...
2 Jun 41min
All Our Dates Are at His House — Should I Be Worried?
Happy anniversary to us — we're recording this one from Miami in the hotel where we took our first trip together five years ago. Jake planned the whole thing, and we almost missed the flight (not our ...
1 Jun 48min
Meeting People IRL, App Burnout & Being Comfortable Being Alone
Allison Lane joins the podcast for a conversation about dating in your 30s, meeting people in real life, and the pressure women feel to have everything figured out by a certain age. From run clubs and...
28 Mai 39min
When a Second Chance Is Worth It (And When It’s Self-Sabotage)
Dr. Joy Burkheimer joins the podcast for a conversation about second chances, relationship “redemption arcs,” and whether people can actually change after hurting someone they love. From attachment st...
26 Mai 48min
Is It a Red Flag If You Never Fight With Your Partner?
We're both sick, we slept until noon, and we have a mystery anniversary trip in two days — Jake planned the whole thing and Ilana has no idea where they're going. We talk froyo orders (gummy bears are...
25 Mai 41min
I Thought Hitting My Goals Would Feel Different
For so much of my life, I thought certain milestones would fundamentally change me. The relationship, the career growth, the apartment, the race finish line, the goals I spent years chasing. I thought...
21 Mai 47min
