Jun 18
"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 watching friends get engaged while she's still navigating first dates, the pressure of ... Show More
42m 7s
Jun 15
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 difference between giving someone grace and making excuses for them, whether having a gr ... Show More
43m 2s
Dec 2024
260. The BEST dating advice for your 20s ft. Dateable podcast
When it comes to dating in our 20s, the entire experience seems like a bit of a maze and often leaves us questioning, is there a RIGHT way to be dating in our 20s? Should I be playing it casual, and just having fun, prioritise being single and getting to know myself, only dating ... Show More
47m 38s
Aug 2025
136. Hot Not Bothered Summer: Dealing with Rejection, Dating Droughts, and Friends Who Don’t Get It
Welcome to the last Hot Not Bothered episode! Jess and Caroline tackle some difficult WHATADOs, answering questions about how to date after trauma, how to approach being the only one in your friend group who’s dating, and how to accept being “too much” in the dating world. Plus, ... Show More
1h 13m
Dec 2024
Is It Too Early To Be Annoyed With The Person You’re Dating?
Why won’t Jared go to therapy? We get this question often and, this week, he shares his own thought on why as well as a helpful TikTok, "Men Who Wear Masks And Struggle With Conflict" by @elisemicheals. Plus, he and Jordana are slipping more into f*ck it mode for the holidays. Th ... Show More
1h 7m
Happy Thanksgiving! In this episode I answer listener questions about how to enjoy the holidays when you're single, how to get over a situationship when you're in the same friend group, what to do if the idea of going on a date causes so much anxiety, tips for bonding with your significant other's family, advice for believing your healthy relatioship is real ... Show More
<p>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.</p><p>My book, "That's Bold of you" is available on Amazon.</p><p>Instagram: @case.kenny</p><br/> <p>Hos ... Show More
