Trudy Walker hated her life. She thought it was totally messed up until she found out about a contest that could change everything...

Freshly engaged Nicole is having second thoughts as she wonders if the one she's really meant to be with is her mystery college pen pal whose letters she has kept all these years.

Following a breakup, schoolteacher Georgia Jackson finds herself in a fake relationship with wealthy playboy Chase Knight a week before Christmas. As they spend time together to outwit the paparazzi, Chase seems to find Georgia’s simpler life and traditions more appealing than his bachelor ways. Is it all a romantic ruse, or are Chase and Georgia really falling in love?

After receiving two separate marriage proposals, Natalie asks the gang to reunite in Peekskill, NY.