In their first episode recapping the past year, the two opened up about parenting teens and dealing with a feeling of distance from their older kids, particularly Oliver and his 15-year-old Wilder.
While talking about missing his eldest being more affectionate and clamoring for attention, it brought to Kate's mind an incident from their childhood.
"Oliver, remember when you were 15 years old and you punched a hole in your room?" Kate recalled, deeming him "so moody," which Oliver clarified was more anger and embarrassment.
"Mom embarrassed me," he said of their mom Goldie Hawn, launching into a story of how his attempts to spend time with a teenage crush were foiled.
"She pulled up in her Rabbit, her Cabriolet. The top was down, she was gonna be great," he recounted. "I was gonna get in the car, we were gonna go 'park'.
"And mom's like, 'Where are you going?' She had no idea, and then mom's like, 'You can't get in a car with this person I don't know!'"
While the 46-year-old admitted his mom was "completely correct," he was still left crestfallen in front of his crush, adding: "I was just devastated, I went and destroyed my room."
Kate continued: "You went in your room, you punched a hole in your wall, and you probably said 'You don't even know who I am anymore.'"
The siblings enjoy a close relationship with their mom now, though, as well as their "Pa" and Goldie's longtime partner Kurt Russell.
Oliver related the incident to how it mimicked his current dynamic with Wilder, who he shares with wife Erinn Bartlett.
"[Wilder] is in this moment right now of teenage, where our relationship has definitely shifted," he explained, adding: "He'll say stuff like 'You don't even know me anymore,' and he's poking me, he knows how to get my goat, even though I know he's joking."
The Nashville star also joked that his son's love language was fighting, saying that he'd kick and scratch, leading his dad to quip: "Will you just hug me, just love me!"
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