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
30, Single, and Happier Than Ever
This week, I’m joined by content creator Annie Jorgensen to talk about what really shifts when you turn 30 and stop looking for someone to complete you. From a major heartbreak (with a cheating ex who...
12 Maj 49min
Waiting for the Other Shoe to Drop & I Have a Big Announcement
Jake's back from Florida with a roulette win and some bachelor party receipts. Ilana has a major life announcement that's been months (or years) in the making.. Two listener questions: does astrology ...
11 Maj 42min
Your Next Relationship Might Be Around the Corner
In this episode, we sit down with Kerry Russo, the creator behind UES Things, to talk about what it actually means to put yourself out there — and why staying in your comfort zone might be the biggest...
7 Maj 41min
Stop People Pleasing, Start Feeling Secure
Trevor Hanson is back for part two, and this episode goes even deeper into people pleasing, anxious attachment, and what it really means to feel secure in yourself. We talk about why even secure peopl...
5 Maj 48min
