It is a sleepless night for everyone. Jen and Sam accidentally meet up when running an emergency errand for Chris and Kris. Jen and Sam try to help with the labor process while also airing out their feelings.

Jen reconnects with Kate at Chris and Kris's wedding, much to Sam's dismay; after a long and stressful wedding prep.

Jen and Sam's “moment” leads to a strained and uncomfortable friendship; Jen attempts to drown her sorrows at a frat party by making out with a 21 year old student.

Jen struggles with her breakup with Gillian; Sam struggles in her relationship with Elizabeth; Jen and Sam have a heart to heart.

Jen breaks it off with Gillian after she realizes Gillian can't sign her divorce papers; Sam's suggestion of the wet-t-shirt contest wins her a management position, but may lose her a girlfriend.

Jennifer's camera is stolen and a sex tape of her and Gillian finds its way to the internet; Sam, fearing Elizabeth only loves her for the sex, fakes an orgasm; Chris bonds with Sheila causing Kris to feel left out.

Jen unknowingly makes a date with one of Gillian's exes to shove her growing feelings for Gillian under the rug.

Jen meets her "Bridge Girl" Gillian through a night of lesbian speed dating; Sam searches for a second job to keep her condo payments up while entering into a more committed relationship with Elizabeth.