It’s Benji’s birthday and Esther and Jeff take him on a road trip full of fun stops along the way. However, Esther’s ulterior motive threatens to derail the celebration.

After visiting a fertility clinic to freeze her own eggs, Esther plans to donate some of her eggs to offset the costs. Meanwhile Benji’s paternal instincts kick in as he awaits word on a sperm test.

When Esther and Benji stand in line for a Kylie Cosmetics pop-up store, Esther tries to avoid the distractions of rabid teenage girls and cutthroat moms while Benji roams off and becomes the man he really is — a guy who owns a saltwater aquarium.

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.

When Esther invites a lesbian couple from her building over for a dinner party to convince them to become her mentors, Benji has to help out so she doesn’t embarrass herself. In doing so, the two women take more of an interest in Benji inciting Esther’s jealousy.

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.

Benji is excited when he is given the opportunity to accomplish a goal that dates back to his old ska band days – to make a music video.

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.