Whitney Claire Kaufman

Phil's birthday coincides with the release of the new iPad, Mitchell is preoccupied with a new desire to toughen up, and Manny and Gloria face off against Jay in the game of chess.

When Reagan (Christina Applegate) loses her engagement ring, a Brinkley family heirloom, Chris (Will Arnett) uses the opportunity to give Reagan the proposal he was never able to give. In order to cover up losing the ring, Regan must seek out her worst enemy – Chris’ grandmother (guest star Marion Ross). Meanwhile, Kevin (guest star Jason Lee) returns and tries to win Ava (Maya Rudolph) back with the help of Julian (guest star Chris Diamantopoulos). Jennifer Hall also stars.