The story explores a five-year relationship between Jamie Wellerstein, a rising novelist, and Cathy Hiatt, a struggling actress. The show uses a form of storytelling in which Cathy's story is told in reverse chronological order (beginning the show at the end of the marriage), and Jamie's is told in chronological order (starting just after the couple have first met). The characters do not directly interact except for a wedding song in the middle as their timelines intersect.
Cathy is sitting alone lamenting the end of her marriage ("Still Hurting"). We shift to meet Jamie. It is five years earlier and he has just met Cathy. Jamie is overjoyed to be dating outside his Jewish heritage ("Shiksa Goddess").
Cathy and Jamie are in Ohio. It is her birthday and he has come to visit her as she works in a show there ("See I'm Smiling"). She is anxious to fix any problems in their marriage but she becomes angry when Jamie tells her he has to go back early to New York. During breaks in the music, we see a younger Jamie, talking to a literary agent about his book.
Jamie is moving in with Cathy. He comments on how lucky he is that everything is going right for him; his book is being published and his life with Cathy seems too good to be true ("Moving Too Fast"). Elsewhere an older Cathy is making a call to her agent: it seems her career isn't going the way she planned it.
Cathy is attending Jamie's book party. She sings about how he ignores her for his writing but she will always be in love with him ("I'm a Part of That").
Jamie and Cathy celebrate their second Christmas. He tells her a new story he has written about an old tailor named Schmuel and he gives her a Christmas present: a watch, promising to support her as she follows her dreams of acting. ("The Schmuel Song").
Cathy is in Ohio and writing to Jamie. She describes to Jamie her disappointing life in Ohio among her eccentric colleagues ("A Summer in Ohio").
Jamie is sitting with Cathy in Central Park. Jamie proposes to her and, for the first time in the musical, they sing together ("The Next Ten Minutes"). They get married, exchanging vows to stay together forever.
Jamie is facing temptation from other women, especially now his career as a writer has escalated ("A Miracle Would Happen"). Cathy, meanwhile, is auditioning for a role("When You Come Home to Me"). She is getting down about the rejection she faces as an actress and complains to Jamie ("Climbing Uphill").
Jamie speaks to Cathy on the phone, trying to convince her that there is nothing going on with him and his editor, Elise. He wants to celebrate a book review but Cathy refuses to go out.
Jamie is fighting with Cathy, trying to get her to listen to him. He accuses her of being unsupportive of his career just because hers is failing. Though his words are harsh, he promises her that he believes in her ("If I Didn't Believe in You").
A younger Cathy is in the car with Jamie, who is going to meet her parents. She tells him about her past relationships and hopes not to end up in a small town life like her friend from high school ("I Can Do Better Than That"). She asks Jamie to move in with her.
Near the end of the relationship Jamie wakes up beside another woman ("Nobody Needs to Know"). He tries to defend his actions and blames Cathy for destroying his privacy and their relationship. Jamie promises not to lie to this woman and tells her that "I could be in love with someone like you," just as he does to Cathy in "Shiksa Goddess."
Cathy is ecstatic after her first date with Jamie. She sings goodbye ("Goodbye Until Tomorrow"). She proclaims that she has been waiting for Jamie her whole life. Simultaneously but five years forward, Jamie sits in their shared apartment writing laments over the relationship ("I Could Never Rescue You"). As Cathy waves Jamie "goodbye until tomorrow", Jamie wishes Cathy simply "goodbye".
The musical style draws on a number of musical genres, including pop, jazz, and classical, klezmer, Latin, Rock, and Folk. The orchestration consists of piano, guitar, fretless bass, two cellos, one doubling on celesta and tubular bell, and violin, doubling cymbal."Still Hurting" - Cathy"Shiksa Goddess" - Jamie"See I'm Smiling" - Cathy"Moving Too Fast" - Jamie"I'm A Part of That" - Cathy"The Schmuel Song" - Jamie"A Summer in Ohio" - Cathy"The Next Ten Minutes" - Jamie & Cathy"A Miracle Would Happen/When You Come Home to Me" - Jamie/Cathy"Climbing Uphill/Audition Sequence" - Cathy"If I Didn't Believe in You" - Jamie"I Can Do Better Than That" - Cathy"Nobody Needs to Know" - Jamie"Goodbye Until Tomorrow/I Could Never Rescue You" - Jamie & CathySource: MTI Shows song list
The show debuted at Northlight Theatre in Skokie, Illinois in 2001, running from May–July 1. The production starred Lauren Kennedy as Cathy and Norbert Leo Butz as Jamie. Kennedy had a previous commitment (a role in South Pacific in London) and was replaced by Sherie Rene Scott. Scott, therefore, performed the vocals on the cast recording.
The show opened Off-Broadway at the Minetta Lane Theatre on March 3, 2002 and closed May 5, 2002. Directed by Daisy Prince, Butz and Scott again starred. The production won the 2002 Drama Desk Award for Outstanding Music and Lyrics, as well as receiving Drama Desk nominations for Outstanding Musical, Outstanding Actor, Outstanding Actress, Outstanding Orchestrations, and Outstanding Set Design. It also received the Lucille Lortel Award nomination for Outstanding Musical and Outstanding Actor, and the Outer Critics Circle Award nomination for Outstanding Off-Broadway Musical.
The show was revived in 2013 Off-Broadway at the Second Stage Theatre for a limited engagement with Adam Kantor and Betsy Wolfe in the roles of Jamie and Cathy, respectively. Brown himself directed. In March 2015, Kantor and Wolfe reprised their roles in a two-night-only concert production of the show at the American Conservatory Theatre in San Francisco.
The show premiered in Paris, France in 2013 presented by American Musical Theatre Live featuring Jonathan Wagner as Jamie and Miranda Crispin as Cathy.
The show was given its Irish Premiere at The Lyric Theatre, Belfast in 2015, running for a limited engagement. It starred Fra Fee as Jamie and Amy Lennox as Cathy. The production was directed by Stephen Whitson.
On September 12, 2016, Jason Robert Brown, along with SubCulture, had a one night benefit for the Brady Center to prevent gun violence. The Town Hall at 123 W 43rd St hosted this event. Cynthia Erivo played Cathy and Joshua Henry played Jamie. Jason Robert Brown directed the orchestra.
On October 28, 2016, Samantha Barks and Jonathan Bailey took on the roles of Cathy and Jamie on the West End in London for the first time.
An adaptation starring Anna Kendrick and Jeremy Jordan was directed by PS, I Love You director Richard LaGravenese. The film was premiered at the 2014 Toronto International Film Festival.