The movie plays out over the years, all featuring one day July 15th.
The movie opens up briefly on July 15th, 2006, with Emma Morley (Anne Hathaway) swimming and then riding a bike. Then the numbers flip back to July 15th, 1988.
1988: Emma and Dexter (Jim Sturgess) are celebrating their college graduation with friends, still wearing their caps and gowns. Dexter introduces himself to Emma, and she says they’ve already met, a couple of times, but he was drunk. He offers to walk her home, and they start making out at her door. She gets nervous, and he says that they can just be friends, so they curl up in her bed and go to sleep. She asks if he wants to do something with her that day (it is already the early hours of the morning).
1989: Dexter helps Emma move into a dumpy apartment in London. They talk about her desire to become a writer. Dexter has to leave for India.
1990: Emma is working at a Mexican restaurant. She starts showing the new guy, Ian (Rafe Spall), the ropes and calls the restaurant “the graveyard of ambition”. She talks to Dexter on the phone, and says she’s not writing because being a waitress is what she does now. He tells her that she needs to keep writing, and that “nothing truly good was easy”. She asks who said that and he reminds her that she told him that once. They talk about Dexter teaching, and she cautions him not to sleep with his students. Dexter agrees, and we see that there is a young girl jumping around on his bed, naked. They get disconnected. Dexter goes to meet his mother for lunch (Patricia Clarkson). She chides him for being late, and they talk about when he will really start doing something. He says he likes being a teacher. She asks about the girl who sends him all the long letters; he tells her that Emma is just a friend. She tells him that she wants to talk to him alone at lunch the next day. He asks what it is about, but she doesn’t tell him. They walk to meet his father.
1991: Emma is still working at the Mexican restaurant. Dexter is there with another girl but came to see Emma. She tells him that she was just offered the manager position because they wanted someone who won’t go anywhere. He tells her to walk out the door and never come back. Dexter says no one knows everything about their life when they are 25; she says that he does. He tells her that she is smart and beautiful and capable of anything. Dexter says that if he could give her one thing it would be confidence. He tells her what she really needs is a vacation.
1992: Dexter and Emma are in a car headed to France for vacation. She says she can’t believe that she is really doing this with him, and that they need to have some ground rules. Rule #1: No shared beds, no snuggling. Rule #2: No flirting, no starting anything. He has a girlfriend, and they just can’t go there. Rule #3: No nudity. No seeing each other in the shower, no see each other “wee”, no weeing in the shower. And no skinny dipping. He says that he gets a rule then, and that Rule #4 is no Scrabble. She protests that she loves Scrabble and he hates it, and he says that’s why it is his rule. While at the beach, he helps her put on sunscreen and she notices he has a yin/yang tattoo on his ankle. He says it is the “perfect union of opposites”, and she says that it more like a road sign and it means he should wear socks. They are silent and share a moment, just a look between them. They notice that it is a nudist beach, she tells him not to get any ideas. Later they are at a bar, and after several drinks she tells him that she used to have a crush on him, back when he first spent the night with her after graduation. Dexter tells her that he figured that out, due to the epic letters and “compilation tunes”. He asked what happened, she tells him that she got to know him and that it cured her of liking him. She tells him that they’ve had enough to drink and they leave. Dexter jumps into the water, naked, and convinces her to skinny dip. He confesses that he cares for her, too, but that he “fancies” lots of women, all the time, like he’s just been released from prison. Dexter goes on to say that he isn’t ready for what she would be ready for, but if she’d like to, then can have fun. She dunks him, telling him what she thinks of that. As he surfaces, he sees two guys steal his clothes. He chases after them, literally crying about his stolen Calvin Klein underwear. As they fall asleep in the same bed, Emma asks Dexter how many rules they’ve broken. He says all of them, but she points out they haven’t played Scrabble. He tells her maybe tomorrow.
1993: This year opens with Dexter hosting a cheesy television show. After the show, he calls Emma while either drunk or high to tell her that he likes her beautiful body. She begs him to go home and go to bed, as it is around 5 a.m.
1994: Dexter is in the shower, looking very sick and jittery. He picks up a videotape and present and leaves his apartment. He drives a fancy car to his parents’ home, and his father asks him why he is sweating and that his mother is in her room and has been waiting for him all morning. He finds her, and it is obvious that she is very ill with cancer. He gives her the present, telling her that it is from Emma. It is books. His mother says that is awfully ambitious and tells Dexter that next time Emma should pick short stories. Dexter protests her talking that way. He shows his mother the tape of him hosting his show. She asks why he would do this when he could be doing anything. They argue and she apologizes, and says that she needs to rest. Dexter tells her that he can’t stay, he has to be at the premiere of Jurassic Park. She is obviously disappointed and Dexter has to carry her to her bed. He goes to lay down in his childhood bedroom, and his mother wakes him up hours later, telling him that his father is mad that he wasted their family day. She tells Dexter that she thinks he will end up being a very good man, but he’s not there yet and she doesn’t really like who is right now. His father takes him to the train station, saying he can get his car back when he’s sober, and that if he ever shows up like that again, he will shut the door in his face. Dexter tries to call Emma, but says he remembers that she is out on a hot date. Emma is shown leaving a theater with Ian, who is an aspiring comedian, and over dinner you can tell she doesn’t think he’s that funny. She tells him that she just wanted to celebrate becoming a teacher with someone, and he asks if Dexter was busy. They leave the restaurant and he asks if she wants to go to his place, and they race each other there in the rain.
1995: Emma is dating Ian and teaching at a school. Dexter is hosting a program called “Late Night Lock In” where his father visits him and it is mentioned that his mother has passed away. As his father leaves, he tells Dexter not to pay attention to what the papers are saying: there’s an article stating that Dexter is “The Most Annoying Man on Telly”. We see Emma’s students in a school play with Ian there to root them on, then later Emma watches Dexter do very badly on his show.
1996: It is clear that although Ian and Emma now share a flat, she is disillusioned with him, as he is a deadbeat not earning money and not even working on their home like he promised. Emma goes out to meet Dexter at a posh club. He asks how her relationship with Ian is, and she kind of jokes that it is fine. Dexter goes to the bathroom and does some drugs, and when he returns he insults her job as a teacher. She curses at him and leaves. Dexter chases after her. Emma yells at him that she hasn’t seen him sober in three years, and that she really needed to talk to him about being stuck in a relationship with a man she doesn’t love. She knows he’s been through a lot, what with his mom dying, but she can’t even talk to him, and if she can’t talk to him, then what is the point? She storms off and he asks if they are “breaking up”. She comes back, hugs him, and tells him that she loves him, but she doesn’t like who he is anymore. She turns and leaves Dexter staring after her.
1998: Ian is shown with a scruffy ponytail, hosting a show about video games. He is told that he is being let go. He says he is 32 and doesn’t know what to do with himself.
1999: Dexter is pacing, practicing saying I love you. We then see he’s with his new girlfriend Sylvie (Romola Garai) and her family, most of whom are in the pool, sipping drinks. They then decide to play party games, during which Dexter accidentally bloodies Sylvie’s nose, causing her family to call him a wanker. Emma is then shown going into her flat, which Ian has broken into. He is drunk sitting on the couch, and complains about how she broke up with him whenever he proposed because she was in love with her best friend, which he knows since he has been reading her poetry. She becomes very angry with him and they fight. After they calm down, he tells her that her poetry may be awful, but she is a very funny writer and should pursue it.
2000: Emma, alone, and Dexter, with Sylvie, are attending a mutual college friend’s wedding. At the reception, Sylvie asks if he slept with the bride because they have been attending so many weddings and Dexter has at one point slept with all of them. Dexter denies it. We see Dexter talking to an old college friend who has struck it rich and seems to be offering Dexter a job because he hasn’t seen him on TV in a while. Dexter makes a snide remark about the guy being poor in college, all while staring at Emma. Dexter pulls Emma aside, and they go off together to talk. He gives Emma a wedding invitation he is having a shotgun wedding. Emma can’t believe he is getting married and becoming a father. Emma then tells him that she has been given a modest advance to write a book. Dexter is very excited about it and proud of her. Dexter tells her that even though Sylvie doesn’t like to laugh, he worships her. Emma says she’s happy for him and they share a friendly kiss.
2001: Dexter is shown working a low-level cooking-type job for the college friend he insulted at the wedding. The friend tells him that it isn’t personal and that everyone has to start at the bottom, and Dexter tells him that he enjoys the job. Then Dexter is at home with the baby, where Sylvie is getting ready to be gone until the next day for a hen party. The baby, Jasmine, cries and cries, until he finally gets her to calm down by putting on a play with stuffed animals and reading the baby Emma’s now-published book. Sylvie calls to check in, and we see that she is actually cheating on him with his boss.
2003: Dexter is on a train traveling to Paris, where Emma now lives. She meets him, and they talk about him being divorced. He starts to tell her how he feels, but she stops him, saying she has met someone. He is very upset. They allude to the fact that they slept with each other (presumably in 2002, which wasn’t shown). She says she was just trying to help him get over Sylvie, even though it was one of the best nights of her life. She tells him that they are going to listen to Jean Pierre, her new boyfriend, who is a jazz pianist. As soon as Dexter sees the boyfriend, he tells Emma he can’t do this, and will leave in the morning. Emma is saddened, but goes to Jean Pierre. After listening to him for awhile, she runs to find Dexter, who has been wandering the streets. She tells him that she “thought she was rid of him” and that if they are going to have a relationship, he can’t mess her around or break her heart. He agrees, and they begin to kiss passionately.
2004: Dexter is opening a small restaurant and is practicing his speech for their wedding. Emma comes in and he tells her not to listen to it it’s a surprise. They are obviously very in love and happy.
2005: Sylvie drops Jasmine off with Dexter, and it is clear that they are now friendly with each other, and that Sylvie is now with Dexter’s old boss. Sylvie tells him that she is happy for him, as it obvious he is happy with Emma. That night, Emma tells Dexter she wants to have a baby with him. He tells herthat they should start trying now.
2006: Emma and Dexter have a small argument and she tells him that she’s not pregnant. Dexter tells her that they can try again. She tells him that she’s sorry about the fight, and Dexter suggests they go out for a special evening and then they can get back to it. She agrees, saying she’ll meet him after swimming. Emma is shown writing, then swimming. She leaves a message for Dexter apologizing again for being grumpy and that she’ll be a little late. Emma is then shown riding her bike, when she is struck by a trash truck. As she lies dying, Dexter is smiling as he listens to her message, unaware of what has happened. Dexter is then shown crying, lying in their bed.
2007: Dexter is at a club, trying to provoke a fight. He is badly beaten and stumbles home, only to be found by his young daughter. Sylvie shows up, helps him up, and then drives him to his father’s. His father asks him if this is going to be an annual thing for him. His father then tells him that he should try to go on as if Emma were still living. Dexter says he doesn’t think he can, but his father tells him that he can he’s been doing it for the past ten years.
2009: Dexter is at his shop, looking a little gray around the temples, but in pretty good spirits. Ian comes in and tells Dexter that he hates today. Ian says the day was always there, just waiting to be the day that Emma would die. Ian tells Dexter that he has given up comedy, is now in insurance, and his wife and two kids are outside. Ian tells Dexter that he used to hate him because Emma lit up for Dexter in a way that she never did for him. Ian says that Emma made Dexter decent, and that in return, Dexter made her so happy. Dexter asks if Ian wants to keep in touch, but Ian says that’s not necessary, hugs him, and then goes out to his family. Dexter watches them, smiling.
Back to 1988: The movie then flashes back to the morning after they fell asleep together. Dexter tries to shrug off hanging out with her, saying his parents are coming. Emma says that’s fine, he can leave. He sees she is disappointed, so he tells her that his parents won’t be there quite yet, and she suggests a walk. As they walk, she tells him that she doesn’t want his number, his postcards, or long letters, that they can just be good friends. But if something happens between them eventually, so be it. Dexter struggles up the hill, complaining about wearing the wrong shoes. He suggests they go back to his place, and she tells him that she’ll race him. They run down the street, only to see that his parents are early. He introduces Emma, and she shakes their hands and then his, telling him to have a nice life. Dexter’s mother asks if he is wearing the clothes from the day before, his father calls him a dog, and he tells them that Emma is just a good friend. Then he races after her, asking for her number. She starts to give him her number, her parents’ number, her address, her father’s work fax number… He tells her that he only needs her phone number. They share a big kiss, after which they tell each other goodbye multiple times and he watches her walk away.
2011: We see the ghost of the past as 1988 Emma and Dexter race each other down the hill, as present day Dexter and Jasmine climb it. Jasmine asks if he ever went there with Emma and he tells her that they did once. Jasmine asks if he misses Emma, and he tells her that he does and that she was his best friend. Jasmine asks who his best friend is now, and he tells her that it is her. Dexter asks who Jasmine’s best friend is, and she tells him that it is probably her mother. He asks what she thinks about him, and, smiling, she tells him that she won’t answer that because he knows what he is. They lie there together on the hill.
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