Ally, a final contestant on a dating show, must face her high school sweetheart when she is chosen for the Hometown Date.
| Actor | Role |
|---|---|
 Italia RicciAlly | Ally |
 Chad Michael MurrayBrett | Brett |
 Jack TurnerTanner | Tanner |
 Aliyah O'BrienLauren Burns | Lauren Burns |
 Teagan VinczeHelene | Helene |
| WWanda CannonMolly Wilson | Molly Wilson |
 Michael KopsaTom Wilson | Tom Wilson |
 Brittney WilsonRosie | Rosie |
 Trish AllenDarla | Darla |
 Lauren K. RobekTrish Turner | Trish Turner |
 Gelsea MaeJennifer | Jennifer |
 Angela CaseLola | Lola |
 Serge HoudeWalter Sprodling | Walter Sprodling |