The story of New York lawyer Hugo who heads to Milwaukee with his best friend Madelyn to spend the holidays with his mom Kate, who is also in charge of the local Christmas celebrations. Ever the matchmaker, Kate arranges for Hugo to run into Patrick, Hugo’s high school friend and secret crush, who has recently returned after a successful stint in Silicon Valley. As they enjoy the local holiday festivities together, Hugo and Patrick’s attraction to each other is undeniable and it looks as though Kate’s Santa-style matchmaking is a success. But as Hugo receives word of a big promotion requiring a move to London, he must decide what is most important to him.
Maggie and Jack are childhood family friends and now as adults give dating advice together on their popular local radio show. When they find out their show is being shopped around for national syndication, their boss encourages them to introduce their significant others to their families for a live, on-air New Year’s Eve special. Knowing their fathers’ local jazz club, The Magnolia, is struggling financially, Maggie and Jack agree to the special as long as it’s hosted at the club. But when Maggie and Jack are both dumped before the big event, Jack suggests they pretend to be a couple and surprise their listeners with the news during a midnight kiss on New Year’s Eve!
Lifestyle guru and romance expert, Joanna Moret, has developed a fool-proof strategy for ending holiday loneliness and it’s all detailed in her best-selling book, The Love Audit. After appearing on a morning show, she is offered the biggest opportunity of her career—to throw the MacAllen Holiday Gala—and if all goes well she’ll get her own TV show. Little do her fans, or the MacAllen’s, know that she is newly single and can’t seem to apply her principles to her own love life. Joanna asks the morning show producer, Ted to pretend they are a couple or risk being exposed as a fraud.