When an aggressive woman won’t leave Benji’s brother Dean alone, Benji hatches a plan to help her get over Dean – a plan that includes Esther. Things get complicated when the woman takes a romantic interest in Benji while Esther starts to think she and Dean have a real love connection.

Esther throws a sober sleepover party to rekindle friendships she made at a bachelorette party, while Benji tries to move a childhood camp friend out of the friend zone.

While Benji manages his brother Dean’s apartment complex, both Benji and Esther get swept up in the allure of retirement life, until realizing it may not be all it’s cracked up to be.