A struggling actress and her novelist lover each illustrate the struggle and deconstruction of their love affair.
Cathy tells the story backward: beginning at the end of the marriage and ending after they first meet. Jamie tells the story forward: beginning after they first meet and ending at the demise of their marriage. Almost the entire movie is sung, with few spoken words.”
The movie begins at the end of the timeline, with Cathy (Anna Kendrick) sitting at a desk reading a letter from Jamie (Jeremy Jordan), who is not in the scene. The letter describes Jamie’s decision to move out and end their marriage. Cathy sings “Still Hurting,” and doesn’t understand how Jamie can be so sure the marriage is over. Cathy thinks Jamie is blaming all of the marriage’s problems on her, but she thinks he is to blame too, because he has been keeping secrets from her. Throughout the song, we see pictures of Cathy and Jamie as a couple and on their wedding day. Cathy removes a watch, a bracelet, and her wedding rings.
We cut to the beginning of the timeline, with Jamie and Cathy passionately kissing in Cathy’s bed after their first date. Jamie sings “Shiksa Goddess” to Cathy, describing his lifetime of dating Jewish women (he himself is Jewish) and how Cathy is exactly what he needs. Jamie says that Cathy could have many “undesirable” traits (in jail, actually a man, shaved head, etc), but he wouldn’t care as long as she wasn’t Jewish. He says he could fall in love with someone like her.
See I’m Smiling
This song takes place right before “Still Hurting.” Jamie is visiting Cathy in Ohio, where she is performing in the theatre program for the summer. Cathy sings “See I’m Smiling,” where she insists their marriage will be okay because she is smiling and they are laughing together. Cathy is pleasantly surprised Jamie came to see her and things seem to be going well until Jamie tells Cathy he can’t stay the weekend. Cathy tries to stay positive and be excited about their night together, but Jamie says he can’t even stay the night. Cathy gets mad that Jamie is choosing a party over her, especially on her birthday and when she is performing in a show, when he is constantly going to parties. Cathy mocks his big ego — a result of becoming a successful novelist at 28 and hints to him cheating on her. Jamie does not comfort Cathy.
Moving Too Fast
Soon after the beginning of their relationship, Jamie is writing near the Statue of Liberty when he receives a call from an agent wanting to meet with him about a book he has been writing. Jamie rides his bike to meet the agent and sings “Moving Too Fast.” He can’t believe how well his life is going — he is in love with Cathy and he is signing with an agent. He calls Cathy and says he wants to move in with her, so she should find an apartment for them. Jamie is extremely excited about how successful he is at just 23. We also meet Alise, who will be Jamie’s editor.
A Part of That
Before the events in “See I’m Smiling,” we get to see a glimpse into the parties that Cathy was talking about. Jamie has to do a lot of networking and promotion for his book, so Cathy is left alone to answer interview questions about her life with Jamie. Cathy sings, “A Part of That,” and tells the partygoers and writers about how she feels like she is a part of Jamie’s success because she is by his side. Cathy finds the lifestyle tough, but loves it when Jamie smiles at her, which seems to fix the problems.
The Schmuel Song
At their first Christmas/Hanukkah together, Cathy comes back from yet another unsuccessful acting audition and mopes around the house. Jamie sings her “The Schmuel Song,” a story he wrote for her to cheer her up. Schmuel was a tailor who yearned to make a special dress he envisioned. A magic clock grants Schmuel the gift of unlimited time to see out his dream, but Schmuel is reluctant. Finally, the clock convinces Schmuel to make the dress and Schmuel is able to live out his dreams. Jamie tells Cathy that she is Schmuel (to her dismay) and that she is afraid to go out on a limb. He says she can follow her dreams if she just tries. He gives her the watch we see her take off in “I’m Still Hurting,” which represents her own magic clock.
A Summer in Ohio
This song takes place soon after their marriage. Over video chat, Cathy chronicles her life in a regional Ohio theatre, where she works over the summer, in the song “A Summer in Ohio”. Cathy tells Jamie about the various people she has met, including a former stripper with a snake (Jessica Molasky — who recorded Cathy’s part in the Last Five Years demo recording) and other characters. Another actor is coming on to Cathy, but she is married and sincerely tells Jamie not to worry.
The Next Ten Minutes
Cathy and Jamie walk through the park and we hear Jamie’s half of an insignificant conversation. They get to a gazebo and Jamie sings “The Next Ten Minutes” to Cathy, asking her to share her next ten minutes, or her next ten lifetimes with him. He proposes to Cathy.Cathy says besides being always on time, she will promise to be a good wife and gladly accepts his proposal. They sing together for the first time, since this is the only time their timelines intersect, and they get married.We cut back to Cathy and Jamie walking through the park toward the gazebo, but this time we hear Cathy’s half of the little conversation. It is made clear that the timelines have crossed.
A Miracle Would Happen
Soon after the wedding, Jamie is singing “A Miracle Would Happen” to his friends at a party. He is having trouble resisting the attention of attractive girls, especially since he attends so many parties thrown in his honor as a successful writer. He sees the girls as a challenge to overcome and says he is happy to be married to Cathy.Elsewhere, Cathy is auditioning for her job in Ohio. She sings “When You Come Home to Me,” and the judges, including Sherie Rene Scott, who famously had the role of Cathy in the off-Broadway production, in a cameo here, are impressed with her.Jamie continues to sing “A Miracle Would Happen,” and arrives at his editor’s office. He “sees” the receptionist in just a bra (to imply his temptation) and walks over to his editor, Alise, while she puts on her shoes. It seems like he is having trouble resisting her.Climbing Uphill
We see Cathy on a string of auditions, before her Ohio job, singing “When You Come Home to Me.” The pianist does not get the pace of the song right, and we hear Cathy’s inner monologue, such as, “Why is the director staring at his crotch?” Cathy says she does not want to lead a boring life in the suburbs and wants to be successful as an actress.
If I Didn’t Believe In You
Toward the end of the timeline, Cathy does not want to go to Jamie’s party because she feels abandoned at them. Jamie is angry that she is not being supportive. Jamie sings “If I Didn’t Believe in You” so Cathy could see that he knows she can be successful. He says he wouldn’t be with her if he didn’t know she would do something great. Cathy is refusing to get dressed for the party and Jamie tells her he will not fail so she will comfortable, or lose because she can’t win. He is mad Cathy is making him feel guilty for living out his dream. Cathy exits the room, seemingly unwilling to attend the party.
I Can Do Better Than That
Early in their relationship, Cathy and Jamie are in the car, driving to New Jersey so Jamie can meet Cathy’s parents. Cathy sings “I Can Do Better Than That,” to show Jamie how far she has come in her life. After her best friend got pregnant at a young age, she moved to New York so she could have a better life. She asks Jamie to think about moving in with her (which Jamie replies to in “Moving Too Fast.”)
Nobody Needs to Know
Right before the events in “See I’m Smiling,” Jamie is in bed and tells a woman to wake up, who is revealed to be the receptionist he pictured in a bra during “A Miracle Would Happen” (Jeremy Jordan’s real-life wife). We see Jamie in bed with a woman he met earlier at a party with Cathy, as well. Jamie puts on the same shirt we see him wear in “See I’m Smiling” and tells his various companions that he needs to go visit Cathy, but he wants to stay with “her” (whomever he is with at the moment). Cathy briefly appears, showing that this song takes place over a longer period of time, and he angrily sings to her about how unhappy he is. Finally, we see that he is also with Alise, and he comforts her while she cries, which he did not do with Cathy in “See I’m Smiling.” He tells Alise he can love someone like her, like he said to Cathy in “Shiksa Goddess.” He leaves to visit Cathy in Ohio.
Goodbye Until Tomorrow/I Could Never Rescue You
The morning after “Shiksa Goddess,” Cathy sings “Goodbye Until Tomorrow” to Jamie. She wants him to leave because the moment is perfect and she cannot wait until the next time she sees him. As she walks through the city, she sings about how she has been waiting for Jamie her whole life and she is overjoyed that she found him. She approaches the apartment building we know they will later live in.Back after “See I’m Smiling,” Jamie returns to the same apartment building she is standing outside in the alternate timeline and writes Cathy the letter she reads in “I’m Still Hurting.” As he writes, he sings “I Could Never Rescue You.” Alise has helped Jamie pack his bags and he is leaving Cathy. He says Cathy does not understand how bad their marriage has gotten, but he does not believe it will work. Jamie picks up his bags and leaves the apartment.Jamie and Cathy meet on the stairs, through in different timelines. Cathy sings “Goodbye Until Tomorrow” while Jamie is singing a permanent goodbye to Cathy in “I Could Never Rescue You.”Cathy from the old timeline disappears and the current Jamie sadly walks away. Sometime later, the current Cathy walks up the apartment, presumably to begin the events in “I’m Still Hurting.”