Jenny is assigned a photo shoot with a high-profile Hollywood couple. In exchange for a $2 million donation to their favorite charity, the couple is permitting In Person to print a spread of pictures of their baby. In a fantasy sequence, the baby discusses with Jenny her ongoing relationship problems. Jenny discovers pregnancy pillows hanging in the nursery armoire and realizes the child was born via a surrogate mother. Her plan to expose the parents falls by the wayside after she and the mother engage in a conversation in which the actress reveals how much motherhood means to her. In a parallel story, Ian and Rick vie for the opportunity to father Vivy's child with Jenny as the surrogate, in the hope the stem cells from the umbilical cord can help with Vivy's cancer treatment. The plan ends when Jenny and Vivy mutually agree it's not feasible. Jenny's phone relationship continues as she seeks counsel from the nameless stranger on the other end. In the episode's final scene, Jenny and Ian decide to separate, then fall into a passionate embrace that suggests neither is ready to give up just yet.

Seeking comfort following her breakup with Ian, Jenny impulsively buys an $1800 designer handbag while shopping with her overbearing mother (Susan Blakely). When Vivy vehemently reacts to the purchase as a feeble attempt to compensate for her breakup with Ian by filling her life with unnecessary material goods, Jenny donates the bag to a charity shop. Other plot lines involved Jenny introducing an F. Scott Fitzgerald fan/historian to a carpenter who discovered one of the writer's diaries in an old desk he purchased; the two discover they have something in common when they meet after he sells the diary at auction for $800,000. Becca decides to remain in Los Angeles and invites Ian to dinner; he declines, then changes his mind after he and Jenny have an unpleasant meeting while tending to Vivy after a chemotherapy session. While dining out alone, Jenny calls her phone friend who, unbeknownst to her, is seated at the bar waiting for a take-out order in the same restaurant.