After getting dumped by his girlfriend Maggie, Josh finds himself struggling with the prospect of moving on. His best friend Mike encourages him to get back in the saddle, leading Josh to a chance encounter on a train.
Josh drives himself crazy trying to think of the proper way to ask Laura out via text. He finally works up the courage, but their first date is a total disaster.
Mike convinces Josh to go out for a wild night of clubbing, but Josh finds it hard to work up the courage necessary to approach women.
A trip to Josh's sister Liz's house for dinner turns disastrous when it turns out they've set him up with an unwanted blind date that doesn't understand the concept of boundaries.
Annoyed with Josh's lack of romantic progress, Cupid takes it upon himself to set Josh up with a knockout named Whitney. Unfortunately, Josh's insecurity and jealousy issues threaten the budding relationship.
Josh finally establishes a happy, stable new relationship, but its progress is jeopardized by the return of his ex-girlfriend Maggie. Can Josh resist the urge to take her back?.
Josh and Mike are invited to a lavish destination wedding. The only catches are that the venue for the nuptials is hell itself, Josh's ex-girlfriend Maggie will be there with her new love in tow.
A desperate Josh convinces himself that his new girlfriend Rachel is "the one", and in an effort to prove that theory, volunteers to have them become conjoined twins.
Josh's sister Liz gets dumped by her boyfriend Leo, leading her down a similar spiral into the depths of being single, and allowing her to empathize with her brother's struggles.
Josh obtains some time travel pills from a convenience store, and attempts to prevent his break-up with Maggie from ever occurring. Unfortunately, the course of history doesn't take kindly to being changed.