Sam hates the holidays. Bailey loves the holidays. On a lonely Valentine’s Day the two meet-cute, quickly bond, and become friends. With every passing holiday Sam and Bailey spend together, they fall further in love with each other.
| Actor | Role |
|---|---|
 Mak ShealySam | Sam |
 Alexandra SwarensBailey | Bailey |
| DDanielle MeyerMel | Mel |
| MMaddie SmallMarky | Marky |
| CCatherine BagentKayla | Kayla |
 Joseph MorelandDan | Dan |
 Johanna McGinleyRegan | Regan |
| AAlan TysonDeon | Deon |
 Philip R. GarrettSam's Dad | Sam's Dad |
| JJim AzelvandreBailey's Dad | Bailey's Dad |
| CCaitlin McWethyCodi | Codi |
 Laura RadiJoan | Joan |
 Andrew James MyersBartender | Bartender |
| TTaylor Elizabeth NelsonJen | Jen |
| LLisa CoffeyBailey's Mom | Bailey's Mom |
| JJack RomanSam's Brother | Sam's Brother |
| SSydney AllenBailey's Sister | Bailey's Sister |
| JJacob O'KeefeBailey's Brother-In-Law | Bailey's Brother-In-Law |
| MMatilda BlairFrannie | Frannie |
| EErin HoodlebrinkKatie | Katie |
| JJoan DetrowLisa | Lisa |