Free-spirited Dharma and straitlaced Greg break the news to their respective parents, none of whom are especially thrilled with the match.

While Dharma, Abby and Jane try to help a depressed Kitty struggle through her 50th birthday, Greg, Larry and Edward head off to the slopes to stage their own Winter Olympics. To head off Kitty's stated intention of immediate plastic surgery, the daffy trio persuades her to join them, big wigs and scanty dresses donned, on a mission to flirt at a navy bar. Kitty is an immediate hit - until one of the young men tells her she reminds him of his mother! Meanwhile, tobogganing down a mountainside in a canoe, at night, backwards, turns out to be the father and son bonding experience Greg and Edward never found time for.