NOTE: This spoiler was submitted by Alex

In the 1950s, Sylvie (Tessa Thompson) is waiting outside of a music venue for her cousin Mona, who is late. She spots Robert (Nnamdi Asomugha) and sees surprised to see him. The film flashes back to five years earlier, Sylvie works in her father Herbert’s (Lance Reddick) record store. Robert, an aspiring saxophone player, sees the help wanted sign in the store and has a crush on Sylvie. He asks about the help wanted sign, but Sylvie says her etiquette teacher mother puts it in the window even though they don’t need help because her mother doesn’t want people to think Sylvie works there because they need help. Sylvie says she comes and works there so she can watch TV, and is waiting for her fiancee to come back from Vietnam. Herbert tears up the sign and says Sylvie needs to not watch TV all day and hires Robert.

Robert and his band, the Dickie Brewster Quartet fronted by Dickie (Tone Bell), are playing at the Blue Morocco club for the summer. Robert and his bandmate Dickie are sent drinks at the club by the glamorous Genie (Jemima Kirke), also known as The Countess, who is impressed with Robert’s skill and invites him to a jam session – Dickie says their whole quartet will be there. They go and perform with Genie, who thinks the club is underpaying them, she pays them to get new suits and takes a job as their manager. At the record store one day, Sylvie and Robert accidentally lock themselves in the basement. They discuss music and their lives, and eventually, Robert pulls a bobby pin out of her hair and picks the lock. He invites her to see the band play.

Sylvie and her cousin Mona (Aja Naomi King) go to see the band play. Sylvie is incredibly impressed with Robert’s talent. Afterward, The Countess tells the band she got them a gig at a club in Paris, she just needs to get them out of their contract at the club. The whole band is thrilled except Robert who has come to really like Sylvie. They begin to dance but the club closes for the night. He walks her home and she tells him how she met her fiancee through debutante balls, and that her fiancee is from a wealthy and prominent family. When they arrive home, Robert tells Sylvie when a date happens there’s usually a goodnight kiss – she says no at first, but then agrees, and the two share a passionate kiss. Sylvie’s mother Eunice (Erica Gimpel) sees this, and the next day comes to the store and tells Sylvie she doesn’t want to give the wrong impression – Sylvie tells Robert what happened between them can’t happen again.

Mona has begun dating Robert’s bandmate Chico (Rege-Jean Page) and so they attend a birthday party for Dickie’s wife Carmen (Eva Longoria). Robert ignores Sylvie and is cold to her. Sylvie confronts him and says he shouldn’t have kissed her since she’s engaged, and he points out that he wasn’t the only one doing the kissing. Robert dances with another girl and Sylvie leaves in a huff – he follows her out and asks why she’s so upset that he’s dancing with another girl if the kiss was a mistake. They hear the music from the party in the street and Robert says they should have the dance they missed out on at the club, and so they dance together in the empty street. Sylvie and Robert begin spending time with Mona and Chico, learning more about each other, like how Robert’s mother died and he began working in a factory. Robert and Sylvie eventually sleep together, which Sylvie tells a delighted Mona was “extraordinary”. Sylvie and Robert begin spending all their time together, dating all the time, going to the park, riding bikes, and having picnics, but one night Sylvie comes home and Eunice is waiting for her, furious.

Herbert calls Robert and lets him know he’s been let go. Just then, the band finds out that The Countess got them out of their contract at the club and they’re heading to Paris at the end of the month. Robert can’t get ahold of Sylvie, so he plays the saxophone in the street outside her house. She comes out and he tells her about Paris and asks her to come with him. She doesn’t think it could happen but he makes her promise to think about it. Later, Mona finds Sylvie throwing up in the bathroom, and they deduce she could very well be pregnant. Mona says she needs to tell Robert. On the night the band is supposed to leave for Paris, Robert waits for Sylvie until the last moment when she finally shows up. He’s thrilled until he realizes she’s coming to say goodbye. She tells him she’s his biggest fan – and doesn’t say anything about the pregnancy. He is disappointed but says goodbye and leaves for Paris.

Five years later, Sylvie – who always wanted to work in television – works the phones at a television station, making copious notes all the time. She interviews for a producer’s assistant job on a cooking show, but since she is married with kids the producer Kate (Ryan Michelle Bathe) isn’t sure she can handle the long hours. Sylvie tells her her whole life she has wanted to produce television, and now she knows meeting Kate it is possible for a black woman to be a producer. Sylvie goes home to her former fiancee, now husband, Lacey (Alano Miller). She tells him about the job but he’s annoyed since he has a client coming over for dinner the next night and they had agreed she could only work if it didn’t interfere with her responsibilities at home. Sylvie starts the job and asks the cooking show host Lucy (Wendy McClendon-Covey) if she can take the meal home, and her dinner is a success. Sylvie and Lacey have dinner with his clients, and Sylvie realizes Lacey is being given the contract because the company was found by the NAACP to have discriminatory practices. Lacey is thrilled about the job, but Sylvie says they’re bigots.

Back to the film’s beginning, Sylvie waits for Mona outside of the concert, and sees Robert. He tells her he’s in New York to record an album. When Mona stands Sylvie up, she invites Robert to come to the Nancy Wilson concert with her. He notices her wedding ring, and afterward she gets in a cab and tells him it might be the last time she sees him without buying a ticket. He goes back to his hotel room, only to hear a knock at the door – it’s Sylvie, who tells him after a date there’s usually a goodnight kiss. They sleep together, and Robert asks her to come on tour with him, but she says she can’t because of her daughter, Michelle. Later, Mona calls Sylvie and tells her that she had to go to Atlanta for work with her voter registration work. She tells Mona about what happened with Robert, and says it was just a one-time thing.

Robert’s band goes in to record their album, and The Countess tells them Miles Davis is recording next door and wants to meet the genius behind the band – Dickie assumes it’s him, but it turns out it’s Robert. Robert sends Sylvie a ticket for his show that evening. At home, Lacey gets the family tickets to Disneyworld to celebrate his big account, but Sylvie says she can’t because her job – he tells her to quit since they don’t need the money, but Sylvie says she likes her job. At work, Sylvie notices that off-camera, Lucy is a big, bawdy, raunchy and hilarious person – very different than her on-camera polite personality. Sylvie suggests to Kate they let Lucy be herself, but Kate thinks she would never get past the censors.

The night of the concert, Herbert asks Sylvie if she’s going to tell Robert the truth – she says she doesn’t know. Meanwhile, at work, Kate looks for Sylvie, who isn’t there. Sylvie goes to the concert and sees another woman coming on to Robert, gets upset, and leaves. Robert looks for her and is disappointed she never arrived. When Sylvie gets home, Lacey is upset because she said she had to work late but her boss called looking for her. He knows Robert is in town, but she reassures him. At a New Year’s party, Carmen does a grand performance for the party. Robert wonders why Dickie has a massive mansion and he is still living a normal life, and is told by Sid (John Magaro) the recording boss that they’re Dickie’s songs – Robert points out that they wrote the songs together, but learns Dickie owns the copyright. He gets a call from Herbert, and while he’s on the phone Robert sees Dickie is having an affair with The Countess. Herbert tells Robert there’s something he needs to know.

Meanwhile, at her New Year’s party, Kate tells Sylvie she is engaged and leaving her job – and Sylvie is being promoted to her position as the producer. Sylvie is stunned and goes to look at the office that is now her own. When Sylvie returns home, she learns that Herbert has had a heart attack and died. At the funeral, Sylvie is doing work and Robert chastises her for not being a better host. She says life is too short to not do things you love and tells him she was so grateful that he married her even though she was pregnant that she’s been trying to be the woman of his dreams but she wants to be the woman of her own dreams. He tells her he didn’t marry her because it was noble, but because he loved her. He says he never wanted her to be the woman of his dreams – he wanted to be the man of hers, but he knows that position is filled.

At the recording studio, Dickie continues acting like the boss. Afterward, Chico tells Robert that he has heard from Mona that Sylvie and Lacey are splitting up. Robert runs into some old friends who offer to put in a word for him in Detroit with Motown anytime he wants. Robert goes to Sylvie’s house and tells her his father called him from the hospital the night he died and told him that Michelle was his daughter. He wants to know why she didn’t tell him, and she says she didn’t want to have to make him choose. He says he wants to meet Michelle, and Sylvie agrees – Robert begins visiting Michelle and spending time with Sylvie again, he leaves the band to stay in New York and he and Sylvie resume their relationship.

Robert goes to Sid and tells him he’s ready to start recording as a lead, but Sid tells him jazz is on the way out and that times are changing. Robert wants to provide for his family and calls Chico to see if he’d be interested in putting a group together, but Chico says after Robert left the band he had to take a job that’s going to Europe. Robert calls his contact to see if he can get him a job at Motown, and Sylvie finds success at work just letting Lucy be her wild self on camera. Robert tells Sylvie about the Detroit job and says he hopes they can all move to Detroit as a family after he gets everything set up there. Sylvie hesitates because of her job but says yes. When Robert gets to Detroit, he discovers his contact was just talking a big game and is essentially just an assistant at Motown.

Robert sees Sylvie at work and how much she loves her job. He’s too embarrassed to admit there was no job for him. Sylvie excitedly tells Robert she will be able to get a job with her station’s Detroit affiliate starting at the bottom, and Robert tells her he doesn’t want her to come to Detroit. He claims he’s realized he’s “not a family man”. She angrily tells him to leave immediately. She tells him when he decides he wants to come back, “don’t”. Robert begins working in a factory to make ends meet. Sylvie runs into Carmen who mentions that Robert is working at the auto plant, not Motown as Sylvie thought. Sylvie wonders why Robert didn’t just tell her he didn’t have a job, and Mona points out it’s like her not telling him she was pregnant – he didn’t want her to throw away everything he worked so hard for.

While leaving the plant one day, Robert is stunned to see Sylvie waiting for him. She tells him he can’t be happy without him in her life, and he leaves with her, finally together.

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In the 1950s, Syvlie (Tessa Thompson) is engaged to an away soldier but meets and falls in love with Robert (Nnamdi Asomugha), a musician working in her father's record store. Robert gets a huge opportunity to go to Paris, and asks Sylvie to go with him. Sylvie realizes she is pregnant and doesn't tell Robert so he will not feel like he has to choose. She tells Robert she can't go to Europe and good luck. Five years later, Sylvie is married with a child and reencounters Robert. Eventually, she leaves her husband and Robert learns the child is his. They begin living as a family, but Robert loses music work to stay with them, and eventually travels to Detroit for work. He knows how much Sylvie loves her career in television, so lies to her and says he doesn't want a family because he doesn't want to make her feel like he has to choose. Eventually, Sylvie realizes the truth, goes down to Detroit and finally makes it clear she wants to be with him, and he happily leaves with her.