Jenny McIntyre, a young magazine photographer, learns that her best friend, Vivy Porter, has cancer which causes her to re-evaluate her life choices. Due to Vivy's advice, some strange phone conversations, a talk with one of her photography subjects and her own doubts, Jenny postpones her wedding to Ian.
On her first big writing assignment, Jenny discovers that the story she's been sent to report isn't the true story. She must dig to get information that a couple faked the birth of their child.
Although they've broken off their engagement, Jenny and Ian secretly keep having sex. Jenny gets jealous when Vivy's other best friend, Becca, comes to town to support Vivy. While covering the separation surgery of adult conjoined twins for the magazine, Jenny learns an important lesson.
Vivy gets a tattoo after her first round of chemo therapy. After Jenny buys an expensive purse, Vivy makes her come to the seminar she is giving women on finances. Meanwhile, Jenny has problems with her mother.
While over at Vivy's, Jenny drunk dials "Cell Phone Man" leading to her setting up a meeting time with him. However, Vivy has a bad day of chemo and needs Jenny to come over so she misses the date.
While working on a story on a young acclaimed artist, Jenny learns her father is also an artist. Meanwhile, Becca and Ian take their relationship to the next level. Rick gets involved in the Big Brother program and continues to be supportive to Vivy.
Jenny works on a story on a man who has done research on how people never get over their first love. She looks up her first love and they reconnect, but when he asks her to go traveling with him for a month, she realizes she can't go back. Meanwhile, Vivy deals with menopause symptoms due to the chemo and Jenny and her mother fight again.
After Vivy's revelation that Ian and Becca are sleeping together, Jenny decides to go out on a date with the first person that asks her which turns out to be a much older man. Meanwhile, Jenny is upset that Ian and her father are still restoring a car together.
It's debutant season and Jenny is assigned to cover the "it" girl of the moment, Dylan Graham, but when Dylan purposely gets in trouble with the law, Jenny realizes there's more to the story than meets the eye. Meanwhile, she and Ian kiss and then she feels bad about it and goes to talk to Becca after she reacts negatively when Ian tells her the news. Later, Jenny is there for Vivy when she must cut her hair.
Jenny is shocked when she learns her father has disappeared, leaving only a note for her mother. Meanwhile, she happens onto the cell phone caller at a restaurant, but just misses him. She then looks him up and reconnects with him. At work she covers the story of a woman who talks to people in a coma with the hopes of bringing them back.
Jenny goes out on a date with Brian, the man she believes is the Cell Phone Man. Becca and Ian work on planning the wedding. Meanwhile, at work Jenny photographs a woman, who due to a head trauma believes that her husband has been replaced with an alien.
Jenny discovers that Brian is not cell phone man. Dr. Rain faces charges for testing unapproved medication on herself and leaves town. Vivy learns that Rick is in love with her and Ian and Becca decide not to elope.
Jenny goes to a psychiatrist to help her after finding out that Brian is not cell phone man. The psychiatrist tells her to bury her cell phone and move on, which Jenny does, but regrets and eventually gets the phone back from Vivy.