Whine Down with Jana Kramer

Forget Your Ex! Younger Men Want Older Women!

Whine Down with Jana Kramer

Show Notes

From Kris Jenner to Jessica Simpson, divorceés are dating younger men in their chapter two! Kelly Bensimon opens up about her own liberating experiences with younger men - and Jennie Garth joins to discuss what marrying a man 9 years younger has brought to her life. 

Are there pros and cons to dating younger? They discuss it all! See omnystudio.com/listener for privacy information.

More from Whine Down with Jana Kramer

Oct 23, 2026

Jana, Kathryn and Kristen are diving into the latest headlines and we can’t get over this week’s episode of Dancing with the Stars! The ladies unpack Julia Stiles’ cast reunion of 10 Things I Hate About You, and Jana has an unpopular opinion about Tyler Cameron’s surprise gender reveal. Plus, some hot takes on the Victoria’s Secret Fashion Show! See omnystudio.com/listener for privacy information.

Oct 22, 2026

Divorce Coach Samantha Boss is BACK and ready to give advice to Courtney Robertson while she navigates her public divorce. From parenting plans to how to navigate the upcoming holidays as a single parent, Samantha is giving sound advice because…she’s walked through it herself! Email us at: [email protected] or call us at 844-4-I Do Pod (844-443-6763) Follow I Do, Part 2 on Instagram and TikTok See omnystudio.com/listener for privacy information.

Oct 22, 2026

Listen if you want to… Why is everyone hating on Kylie Jenner as a newly crowned Victoria’s Secret Angel We’ve got reviews, our no filtered thoughts on Widows Bay, Crystal Lake, and You Can See Everything A towel and drawer dilemma that many can relate to at home. Asking for a friend, if you are staying for free in their apartment, should you abide by their rules? See omnystudio.com/listener for privacy information.

Oct 21, 2026

Jana connects with Whine Down listener Amber to share some advice on life with a new baby and dealing with the end of a toxic relationship. Jana opens up about the challenges of co-parenting and shares how to handle questions from kids about a difficult co-parent. Plus, we learn the importance of cleaning “your side of the street”! See omnystudio.com/listener for privacy information.

Oct 18, 2026

Jana heard about a kid who stayed home from school to babysit their younger siblings, which prompts the question… are we asking too much of our kids??

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