A recently single Jessica sends Christmas cards to people who have impacted her life—the aunt who raised her, her younger brother in the military, a popstar who was part of the soundtrack of her life, the music teacher who inspired her, and the best friend who always tells the truth.
| Actor | Role |
|---|---|
 Torrey DeVittoJessica Winthrop | Jessica Winthrop |
 Chad Michael MurrayLuke Wilson | Luke Wilson |
 Lolita DavidovichAunt Lila | Aunt Lila |
 Drew SeeleyJax | Jax |
 David QuinlanJohn | John |
 Kimberley ShonikerMimi | Mimi |
 Lanie McAuleyAngie Dawson | Angie Dawson |
 Madison SmithCarter Winthrop | Carter Winthrop |
 Grant ShowTom | Tom |
 Geoff GustafsonTodd | Todd |
 Theresa WongRuth | Ruth |
 Max ArchibaldJoshua | Joshua |
 Jay HindleWes | Wes |
 Paula GirodayLeslie | Leslie |
 Stephen LoboPrimo | Primo |
 Amara KremblewskiBride | Bride |
 Sei CampbellGroom | Groom |
 Calix FraserBilly | Billy |
 Vera Ann FredericksonDaisy | Daisy |
 Garfield WilsonPerry | Perry |
 Johnny GhorbaniTim | Tim |
 Angus StewartMusic Director | Music Director |
 Ben AffulBouncer | Bouncer |
| JJoe CostaOld Vendor | Old Vendor |
 Kwasi ThomasD.J. | D.J. |
 Carlos FortinJoey | Joey |
 Nikki ChohanWaitress | Waitress |
 Harry HanWaiter | Waiter |