When a womanizing, reality dating TV producer runs into his college crush, he realizes his bar-hopping, bed-hopping ways are leaving him unfulfilled so he has the only woman he ever had feelings for re-train him to become the nice guy he once was.
| Actor | Role |
|---|---|
 Navi RawatGwen | Gwen |
 Dash MihokDave Randall | Dave Randall |
 Ryan FreemanSnotty Student | Snotty Student |
 Brittany DanielKelly Liffen | Kelly Liffen |
 Anya MonzikovaKristen | Kristen |
 Melanie SpechtTom Brady Babe | Tom Brady Babe |
 P.J. ByrnePerry the casting director | Perry the casting director |
 Kevin PeakeLeslie | Leslie |
 Geoffrey ArendRyan | Ryan |
 James LesureClint | Clint |
 Chris CoppolaFreddie | Freddie |
| CCassandra GraeOlivia | Olivia |
 Annie Katsura RollinsMelinda | Melinda |
 Stephen TobolowskyJon | Jon |
 Stacey ScowleyLisa | Lisa |
 Gino Anthony PesiTaylor | Taylor |
 Chrissy MetzBonnie | Bonnie |
 Martha SmithAndrea | Andrea |
 Carla ToutzHippie Chick | Hippie Chick |
 Terence Bernie HinesWilliam | William |