Jenny McIntyre, a photographer for In Person magazine, is days away from getting married, and is starting to have nightmares and become a little bit of a bridezilla. In the middle of her doubts about her own upcoming wedding, she is assigned to work on a story about a woman who has gotten married to three men, in part because she "loves weddings." Jenny leaves the assignment, promising to come back later, and is blindsided when her best friend, Vivy announces that her cancer has returned, and it is in her brain. Vivy demands that Jenny reassess everything in her life, especially her engagement to Ian. Jenny refuses, but over the course of the episode has no choice, as her subconscious starts to provide a running, involuntary reassessment for her. She also connects with a mysterious stranger when she misdials Ian's number.

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.

Assigned a story about a teenaged whiz kid (Cody Kasch), winner of a word definition bee, Jenny succeeds in reuniting him with his estranged mother. She discovers her father's regular deposits into her bank account are the results of investments he made with the money she won while unwillingly participating in childhood beauty pageants at the behest of her mother. Vivy has a date with the visiting editor of In Person's sister publication in Mexico, much to Rick's dismay. Jenny's date with her mysterious phone friend is postponed when Vivy, suffering anxiety due to a partial hair loss resulting from increased chemotherapy treatment, calls upon her for comfort.