Jenny, a photographer with a seemingly perfect life, gets a wake-up call from her best friend that forces her to reconsider her pending nuptials. After dialing a wrong number, Jenny makes a new connection with a stranger.
Jenny uncovers a secret while on assignment covering new celebrity parents, then volunteers to be a surrogate mom for Vivy in the hope that the umbilical stem cells may help cure her cancer. Meanwhile, Ian is increasingly frustrated by Jenny's indecision about their relationship.
Jenny is assigned to cover conjoined adult twins undergoing a separation surgery, and later becomes jealous when a friend of Vivy's visits to offer support. Meanwhile, despite their broken engagement, Ian and Jenny continue an intimate relationship in secret.
Jenny's mother pays a surprise visit. Meanwhile, Vivy gets a tattoo to mark her first round of chemo, and the sexy design shocks Rick.
Jenny agrees to a date with the mysterious Cell Phone Man; Rick is jealous to see a colleague with Vivy, who is starting to show the effects of her radiation treatment. Elsewhere, Jenny learns the reason her father keeps depositing money into her account every month.
Rick signs on to be a Big Brother; Vivy's doctor recommends that she shop for a wig; and Ian and Becca get closer. Meanwhile, the mysterious Cell Phone Man tells Jenny he is falling for her and wants to meet in person.
Upset by Ian and Becca's relationship, Jenny accepts a date with a man old enough to be her father.
Jenny looks up her first high-school love while on a story and takes away from Margot the key to her apartment .Vivy is diagnosed with medical menopause.
Jenny is assigned a profile piece on the debutante daughter of a well-known multimillionaire running for office.
Jenny's father Richard leaves town. Ian spontaneously proposes to Becca. Vivy and Rick plan a road trip to Mexico to buy her expensive cancer drugs. Jenny overhears a nearby conversation and tracks down a man named Brian Fowler who she thinks could be Cell Phone Man.
Jenny goes on a date with Brian, believing he is the Cell Phone Man; Rick and Vivy attend a cancer support group together; and Ian flirts with a colleague as his wedding looms.
Jenny is disappointed after spending the night with Brian for the first time. Later, she suspects he might not be the Cell Phone man when he takes her out for sushi, which she hates.
Jenny learns the mysterious Cell Phone Man's true identity and deals with Ian's looming nuptials. Elsewhere, Rick reveals his feelings to Vivy.