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 Juni 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 Maj 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 Maj 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 Maj 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 Maj 47min
She Thought She Was “Too Much” Until She Met the Right Person
Chloe Hechter joins the podcast for a conversation about everything your twenties are actually filled with: changing career paths, feeling behind, navigating dating in New York City, and learning how ...
19 Maj 49min
Stop Waiting for Him to Confirm the Date & Just Text First
Ilana's recording this one from her deathbed after missing the Brooklyn Half and sleeping the weekend away while Jake walked 25,000 steps to get a burger. Two listener questions this week: a woman wh...
18 Maj 39min
You’re Not Behind, You’re Just in Your 20s
Meg Reynolds is back and we get real about what your twenties actually feel like—uncertain, uncomfortable, and constantly shifting. From turning 27 and questioning everything to navigating dating, fri...
14 Maj 41min
