Are You Settling or Leveling Up?
U Up?4 Jul 2025

Are You Settling or Leveling Up?

This week’s Friday Feels episode gets deep and personal with special guest Case Kenny, author, mindfulness expert, and the man behind the viral quotes shared by Oprah, SZA, and Selena Gomez. Jordana and Jared sit down with Case to talk about his new book The Opposite of Settling and explore why the best relationships amplify who you already are. They dig into what it means to have “out of town confidence,” how optimism and trust shape our dating lives, and why independence is the real secret to intimacy. Then, it’s time for Settling or Settling Up? where J&J get Case’s take on real listener scenarios, from stingy tippers to partners who still text their ex. Can love survive political differences or a forgotten birthday? Case shares why playfulness, clarity, and self-worth matter more than a perfect love story. This episode will shift how you think about dating and maybe even yourself! Watch episode here 👉 https://youtu.be/kfP_MN82co4 Learn more about your ad choices. Visit megaphone.fm/adchoices

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Episoder(808)

My Boyfriend Has a High-Conflict Baby Mama – Help!

My Boyfriend Has a High-Conflict Baby Mama – Help!

It’s a rapid fire episode with 10 relationship questions from YOU, the listeners. Jordana and Jared answer questions about how long is too long to go without sex or a marriage proposal! They discuss w...

30 Sep 1h

She's Older, He's Younger: Is a 7-Year Age Gap Too Much?

She's Older, He's Younger: Is a 7-Year Age Gap Too Much?

It’s autumn, and Jordana & Jared are challenging their listeners to put down their phones, get out of the house, and talk to people! They then get into questions from you and decide if secretly hiding...

25 Sep 35min

My Husband Used AI to Write Me a Birthday Card!

My Husband Used AI to Write Me a Birthday Card!

Jordana discovers her husband used an AI chat to help him write her birthday card, and she has some feelings about whether a love letter still counts when chat gpt edits it for you! Jared and Jordana ...

23 Sep 1h 19min

Dumping Someone in Public: Is It Ever Okay?

Dumping Someone in Public: Is It Ever Okay?

Learn more about your ad choices. Visit megaphone.fm/adchoices

18 Sep 57min

My Boyfriend Won’t Propose Until I Run 125 km!

My Boyfriend Won’t Propose Until I Run 125 km!

Jordana tells Jared how her vacation ended up being the busiest and most unrelaxing, but also the most fun, due to Ronnie the dog getting kicked out of boarding for peeing and joining the family’s cha...

16 Sep 1h 36min

Would You Be a Wedding Crasher If Your Date Asked You?

Would You Be a Wedding Crasher If Your Date Asked You?

Jared and Jordana discovered that you can crash a wedding and think it’s the best way to spend a night out with someone you’re dating! From black-tie dress codes to open bars and live bands, it’d prob...

11 Sep 38min

I’m ICKed Out Over My Boyfriend Fangirling Over a Tennis Player

I’m ICKed Out Over My Boyfriend Fangirling Over a Tennis Player

It’s Jordana’s birthday, Happy Birthday, Jordana! J&J debate wedding plus-ones, jealous partners, and how much texting is too much when you’re dating. They also dive into a text thread discussion of a...

9 Sep 1h 14min

Lauren Lapkus Has a Dating App Imposter

Lauren Lapkus Has a Dating App Imposter

Lauren Lapkus joins Jordana and Jared to talk about dating actors, marriage, kids, and whether being good at acting makes someone too good at lying?? The three play red flag or deal breaker, asking La...

4 Sep 34min

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