In Episode 2 of Don’t Tell Daddy, “He’s HOW Much Older?!,” Elisabeth and Chelsea are joined by Troy Berry, co-owner of 4West, for a candid conversation on age-gap relationships, modern dating, and generational power dynamics. From differing expectations to questions of control versus wisdom, this episode unpacks what it really means to date across age lines in today’s world. With both lived experience and honest reflection, the conversation explores how to maintain identity, set boundaries, and build relationships rooted in mutual respect and clarity.
This week on Don’t Tell Daddy, we’re asking the question everyone’s thinking: how big is too big of an age gap?
Joined by Troy Berry of 4West, Elisabeth and Chelsea dive into the realities of dating across generations, where experience, power, and intention don’t always align.
In this episode, we discuss:
Through a mother-daughter lens, this conversation brings both perspective and accountability to the dating experiences many people are navigating today.
At its core, this episode is about knowing who you are and not compromising that for connection.