Situationships, Approaching Someone IRL & Fir...

A 36-year-old single woman shares the reality of modern dating: a year-long casual situationship, dating app fatigue, and the pressure of watching younger siblings get married while you’re still searching for your person. We talk about what it’s like designing engagement rings wh ...  Show more

Misha Brown joins the podcast to talk about her book Be Your Own Bestie and the real work behind learning to like yourself. We discuss why being a good friend to others starts with being a good friend to yourself, the pressure to shrink ourselves, and how shame shapes the way we ...  Show more

After a couple weeks away from the studio and just days after Jared’s special taping, Jordana starts this episode by giving Jared his flowers and catches him up on her girls’ trip as the hosts settle back in. The first email asks for advice for everyone traveling to stay with fam ...  Show more

This week, J & J are fresh off a dinner party together, but Jared’s own awkward encounter at a bar afterwards has him regretting that nightcap martini. After some daydreaming about winter getaways, we dig into the e-mails, starting with a listener who put their friend onto the po ...  Show more

In this episode, I talk about when to take a break from dating. I talk about your sense of self, purpose, and what to do if dating feels like a "need" rather than a choice.

My book, "That's Bold of you" is available on Amazon.

Instagram: @case.kenny

Hos ...

Is there anything more exciting or terrifying than a first date? No other event is so full of hopeful potential as well as awkward dread; It's a weird thing for sure. And then there are the "first date tips" that usually revolve around what to wear and what to eat (or not eat ...