Elizabeth's engagement plans are thrown into disarray when her fiancée's free-spirited brother David returns home. David's unexpected influence prompts Elizabeth to question her life decisions.

Jamie hasn’t told his family that he and his now ex-girlfriend Emily broke up. After an inopportune run-in with Emily at the train station in his hometown, Jamie convinces her to pretend they’re still a couple to avoid ruining Christmas for his family.

Rebecca, a teacher, and Adam, an ad executive are excited to plan their Jewish wedding, but their wedding and future are put into jeopardy when Adam lands a new ad campaign, and their mothers meet for the first time.