Jack (Andrew McCarthy) is an executive in a financial brokerage firm trying to impress the firm’s president, Drew Clayton (Chris Gillett), in hopes of a promotion. However, Jack is dating the fabulously rich and elegant Demi Clayton (Stephanie Mills), who happens to be Drew’s daughter. Although Demi’s mother Clarisse (Jane Moffat) doesn’t necessarily approve of Jack and would prefer her daughter to date a man within their social circle, Jack still plans on proposing. Trying to create the perfect proposal, Jack signs up for dance lessons in preparation for his proposal to Demi at her father’s lavish annual Christmas Dance. But when sparks start to fly between Jack and his dance instructor, Christine (Michelle Nolden), Jack will have to make some important decisions before it is too late.
Still suffering from the ugly-duckling syndrome that branded his youth, Harold White (Eric Mabius) hires Annie Hayes (Brooke D’Orsay), the pretty and popular girl he knew in high school, to be his dating coach and help him shed his wallflower approach to romance. Annie even enlists her friend Kim (Kathy Najimy), a waitress at a local diner, to be Harold’s practice date. Annie draws Harold out of his shell and teaches him to win over a new love interest with the help of their shared passion for classic love songs. But when sparks unexpectedly fly between “student” and “teacher,” both Harold and Annie must learn how to make up for past mistakes if they’re going to hold onto true love. Starring Brooke D’Orsay, Eric Mabius, and Kathy Najimy.
Although she is still upset from a recent breakup, Corrine (Gilsig) happily prepares for her favorite holiday: Christmas! A gifted musician, Corrine auditions for a solo in a community Christmas concert and plays Christmas carols on the piano to patrons of the music store where she works with childhood friend Dave (Abbey). Her holiday season gets an unexpected dose of romance, when Harold (Di Zio), a mysterious new coworker, tries to form a love connection between Corrine and Dave. With Harold’s help, Corrine begins to view Dave in a new light, though she questions Harold’s intense interest in her love life. Unbeknownst to Corrine, Harold is on a Christmas Eve deadline from a higher power to fulfill this holiday fairytale! As the clock ticks down to Harold’s fairytale mission deadline, Corrine must decide if she will open up to Christmas love.
