Speed advice-ing in Washington Square Park.

Brian grapples with self-doubt, despite his many accomplishments as an actor, writer, and filmmaker.

These super close siblings are learning to navigate the new distance between them.

Comic Micaela wonders how to make space for her dreams while keeping up with the daily grind.

Robin and her wife Mary delve into their fears and anxieties with the help of Bill Burke, founder of The... more

How to manage friendships where one person seems to monopolize the airwaves.

Jennifer and her dad Arnold talk about how generational trauma can affect the way you think about money.

Matt opens up about his struggles with recurring depression and the unhealthy behaviors he's turned to when trying to cope.

Tenea talks parenting after a breakup, and whether she's ready to date again.

Why do we sabotage our own success? Meet Michal, a relentless goal-chaser who never lets himself bask in the glow... more

We sit down with Newt, a recent grad facing the challenges of kick starting their career.

Aja Evans, a financial therapist and coach, sheds light on the connections between debt, money problems, and the impact of... more

Hannah, a college student, who finds herself constantly overwhelmed by her packed schedule joins us to talk about juggling multiple... more

Sara and Katie are two sisters embracing life's twists and turns in the year after the loss of their mom.

Ewan is a writer and a music journalist who never sits still. He writes because he loves it, but he... more

Robin’s sister Kim bravely joins to discuss the political chasm between the two sisters.

Deb got lowballed by a prestigious and flush-with-cash company (we’re talking net worth in the billions). When they spoke out... more

Aileen is tired of being in mother f***ing debt. She can’t stop wondering why her family is living paycheck to... more

As the team prepares to come back with season four, we're catching up with previous guests to see how they're... more

Robin and Producer Steph take the show to a bar for live questions from folks with problems enjoying cocktails. We... more