Kim and Grandma Gail are back in New York after a little Florida stint, settling into holiday season real talk with St. Francis Winery. Kim shares how their family can feel like a reality show on Thanksgiving, while Grandma dives into why older generations “just blurt it out”. Together, they break down the biggest tension points of the holidays — from dating questions to appearance comments to political disagreements — and how to actually survive them with humor, thoughtful pivots, and, of course, a good glass of wine.

In The Rewind, they discuss movies that the whole family can agree and bond over during the holidays. The episode wraps up with a Should We Bring It Back? on controversial holiday songs and an Ask Grandma Anything on boundaries, gift budgets, friend drama, and navigating your first holiday without someone you love. 

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Music By: Guy Kelly 

00:00: Introduction

20:25: The Rewind

24:29: Ask Grandma Anything

37:46: Should We Bring it Back?