"I'm 25 and I've Never Had a Boyfriend"
At 25 years old, this anonymous guest has never been in a serious relationship—and while she knows she's not alone, it often feels that way. In this unfiltered conversation, she opens up about watchin...
18 Jun 42min
What Working on The Bachelor Taught Her About Love
Julie LaPlaca joins the podcast to share her journey from longtime producer on the Bachelor franchise to author of The Love Producer. We talk about what really happens behind the scenes of reality dat...
16 Jun 46min
He's Everything I Said I Wanted — But Something Feels Off
The Knicks are champions and Jake may have cried a little. We start there. Then four listener questions: whether therapy actually helped Ilana find Jake (yes, and here's how), how to tell the differen...
15 Jun 43min
The Reason You're Not Getting a Second Date
Cara Ozek joins the podcast for a conversation about confidence, dating, and the small changes that can have a big impact. From style, grooming, body language, and dating app profiles to dating burnou...
11 Jun 33min
Matchmaker for a Serial Rapist (Without Knowing It)
Addie Sellers joins the podcast to share one of the most shocking experiences of her matchmaking career: working with a client who was later convicted and sentenced to 80 years in prison. We talk abou...
9 Jun 43min
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
