Reagan's extreme competiveness comes out at a New Year's Eve game night, much to Chris's embarrassment. Meanwhile, Kevin worries that Ava is ashamed of him and Missy brings an unexpected date to the party.

Reagan becomes determined to secure a coveted spot for Amy at a prestigious preschool. In an effort to win favor with the admissions office, Reagan volunteers to spearhead the school's annual fundraiser and enlists Ava to help her run a charity auction. Meanwhile, when Chris's older brother comes to visit, the two Brinkley boys revert to their old competitive childhood ways.