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.

Jenny is assigned an article and photo shoot about conjoined twins who are about to undergo surgery to separate them. When she arrives at the hospital, she discovers they have decided to forgo the operation, given the odds that one will not survive are fairly high and neither wants to lose the other. Jenny suggests they view the surgery as an opportunity for one to allow the other to live instead of both dying, which is a given without the operation. They follow her advice, and subsequently one dies. A second plotline involves Becca (guest star Ashley Williams), Vivy's friend from San Francisco, who comes to town to spend time with her. Jenny is jealous that she's in the picture, and her feelings intensify when she learns Becca and Ian went out for drinks. Jenny finally takes a stand re: what has become a somewhat ambiguous relationship with Ian and returns her engagement ring to him.

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.

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.

Jenny volunteers to write a story about up-and-coming Vietnamese artist Amh Thuy, but soon discovers her mother's background story is far more interesting. Rick volunteers to be a Big Brother to a young Hispanic boy who hopes to use the program as a means of finding a husband for his mother. He decides Rick isn't a viable candidate when he sees him interact with Vivy and correctly perceives his feelings for her run deep. Jenny discovers her father forfeited a promising career as an artist in order to raise a family. Ian and Becca take the next step in their developing relationship. Jenny's phone friend calls, tells her he thinks he's falling in love with her, and promises they'll meet as soon as he returns from a business trip. Previews of the next episode suggest he may not be the hunk Jenny has imagined him to be.

Prompted by an interview with a doctor who theorizes that one's first love sets one's course in life and lasts forever, Jenny searches for her own. She discovers he's an award-winning photojournalist and contacts him via his website. Coincidentally he's in Los Angeles and the two reunite. He confesses he still has feelings for her and invites Jenny to take a sabbatical from work and travel with him around the world. She accepts, then declines after giving the matter more thought. Vivy is diagnosed with medicinal menopause and her doctor prescribes unusual treatment to counteract the symptoms. Rick meets with Jenny's mother and is amazed to find her blatantly flirting with him. (Note: Try to Remember, the 8th show in production order, was aired out of sequence, as the 7th[7])

It's debutante season, and Jenny is assigned a story about Dylan Graham, a young debutante at UCLA and daughter of a gubernatorial candidate. While trying to figure out what is disturbing the deb, she meets with her father for lunch, on his birthday. Her father is reticent, though he appreciates her gift of a camera, and hints vaguely that he is about to make a change in his life. Jenny meets with Vivy, Rick, Ian and Becca to have drinks and dinner before going to cover a 'pre-deb party' of Dylan's. Becca, trying very hard to impress, burns dinner while comparing Jenny's poise to 'Jackie O'. Jenny heads to the party, and, in the middle of it, Dylan is arrested for stealing several thousand dollars of merchandise while being videotaped. As she is bundled into the car, she asks Jenny to take a picture of her. Confused by Dylan's behaviour, Jenny turns to the photographs she took of her, and in them, Dylan confesses to being in love with her best friend, Hannah. Meanwhile, Jenny's father has given Ian the Mustang that they had been working on. Concerned, he goes to see Jenny, and they wind up in bed together, but Jenny stops things before they do more than kiss. Jenny speaks to Dylan, and tells her to live her life in a way she won't regret. Ian confesses to Becca about the incident with Jenny, increasing her doubts that she can't keep up with his history with Jenny. Jenny apologizes to Becca, and Dylan meets with Hannah (shot silently, at a distance, while a song by The Indigo Girls plays). Mr. McIntyre leaves a note that reads 'Margot' on a workbench, and drives off on his motorcycle.

Ian's proposal startles Jenny, Rick crosses a line trying to help Vivy, and Jenny gets one step closer to Cell Phone Man.

Jenny is assigned an article on a woman who has filed for a divorce, believing that her husband's body is possessed by an alien. Brian (guest star Ian Ziering) tries to tell Jenny that he is 'not who you think I am,' and reveals he is separated from his wife, and has two children.

First part of the Season Finale. Dr. Raines is to be the subject of an In Person Magazine article on heroes when she goes missing, wanted as a result of trying several experimental anti-cancer treatments on herself without approval.

Second part of the Season Finale. On the advice of her psychiatrist (guest star Carrie Fisher), Jenny buries her cell phone and attempts to forget 'Cell Phone Man'. Rick assigns her a piece for In Person on a blind man who is restoring classic music pieces for digital use. When her psychiatrist recommends she make an effort to stop seeing things that aren't there as she develops her pictures, she turns to him, and he tells her not to let anyone give up her gift. Cell Phone Man (Steven Weber is revealed) returns from China and has his sister, a police detective, trace Jenny's phone. He shows up at In Person, where Becca is using Jenny's phone. Becca refers to her fiance, Ian, and Cell Phone Man, believing Becca to be Jenny, and that she is back with Ian, leaves. After Jenny ceases to see the psychiatrist, Vivy reveals that she unburied Jenny's phone, giving it back to her when Jenny comes to help her makeup at the wedding. Cell Phone Man shows up at the wedding, and objects during the ceremony. Jenny overhears him, and reveals herself from the back of the church, leading him outside. In each other's arms, Cell Phone Man introduces himself as 'James', and they kiss.