Ready to quit the dating scene altogether, burned-out Leah accepts her grandmother's outrageous challenge—40 dates in 40 nights in exchange for a year's rent—only to discover amidst the awkward dinners and unexpected sparks that her biggest obstacle to love is herself.
| Actor | Role |
|---|---|
 Bailee MadisonLeah Jones | Leah Jones |
 Joel CourtneyMason | Mason |
 Jack SchumacherJackson | Jackson |
 Luxy BannerBianca | Bianca |
 Eric NelsenBuzz | Buzz |
 Liz MikelEdith | Edith |
 Jennifer GriffinTilda | Tilda |
 Jai RodriguezSteven | Steven |
 Annie PottsGigi | Gigi |
| JJoseph RosaMatt | Matt |
 Bethany GeaberMavis | Mavis |
 Jeremy CulhaneGeorge | George |
| TTanner EllisBen #2 | Ben #2 |
| MMika IrelandScarlett | Scarlett |
 Mia ChallisVeronica Summers | Veronica Summers |
 Randy McDowellBaker | Baker |
 Mark HapkaCurt | Curt |
 Sterling KnightDate #2 - Potato Guy | Date #2 - Potato Guy |
 Aaron ValentineDate #4 - Pudding Guy | Date #4 - Pudding Guy |
 Ian HylandDate #5 - Spaghetti Boy | Date #5 - Spaghetti Boy |
| AAbid KhanDate #7 - Cat Photos | Date #7 - Cat Photos |
 Blake RichardsonDate #29 - Nuzzle Guy | Date #29 - Nuzzle Guy |
 Tony RobinetteDate #20 - Whiskey Guy | Date #20 - Whiskey Guy |
 Brady BoxDate #38 - Tennis Guy | Date #38 - Tennis Guy |
| KKathryn HowardTammy | Tammy |