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!