When the group settles on a date for their holiday party, it happens to fall on what Mr. K believes will be the end of the world. Ryan invites Anne along on his annual trip to wine country with Steven and Lauren worries her boyfriend is ready to pop the question.

Despite Carrie's warning, Ryan wants to get his first date out of the way and asks Carrie's flaky friend, but not without a little competition from Shaun White. Meanwhile, Yolanda starts a new job at the hospital where Sonia works and tries to reinvent herself.