Cal is initially resistant to Jacob's advice on how to pick up women, but eventually he starts to embrace his new persona and begins dating multiple women. Meanwhile, Cal's teenage son Robbie is in love with his 17-year-old babysitter Jessica, who in turn has a crush on Cal. Cal tries to navigate his own love life while also dealing with his son's romantic troubles.
As Cal starts seeing success in the dating world, he begins to question if he truly wants to continue down this path or if he still holds onto hope of rekindling his relationship with Emily. At the same time, Emily struggles with her own feelings and the consequences of her infidelity.
As the various storylines intertwine, the characters must confront their own insecurities, fears and desires in order to find happiness and true love. The film explores themes of forgiveness, redemption, and the complexities of relationships in a humorous and heartfelt way.