The film opens on a flashback of Gordon (Colin Quinn) telling his two daughters Amy and Kim that he and their mother are divorcing because monogamy isn't realistic.
We jump to today and see present day Amy (Amy Schumer) hooking up with a random guy. She asks him to go down on her, which he does - and after which Amy immediately pretends to fall asleep. We see a montage of her life - getting drunk, getting stoned, partying, and with lots of guys - even though she's sort of already dating Steven (John Cena). She wakes up one morning in Staten Island and has to take the ferry back to New York in full walk of shame mode.
Amy gets back to her life - she works at S'nuff, a snarky men's magazine. After telling her coworker Nikki (Vanessa Bayer) about last night, she goes into a work meeting where her boss Dianna (Tilda Swinton) asks for pitches for new articles. One of her co-workers pitches an article about a sports doctor, Aaron Conners (Bill Hader). Amy makes fun of the idea, saying sports are stupid, and she thinks anyone who cares about them is a lesser person. Dianna thinks that Amy's take on the article will be the most interesting and assigns the article to her, despite the fact that she doesn't even want it.
Amy goes to her dad's house to help her sister Kim (Brie Larson) pack the place up - Gordon has really bad multiple sclerosis and has moved into an assisted living home. Kim is married to Tom (Mike Birbiglia) and has a stepson, the dorky Allister, who annoys Amy like crazy - she's not good with kids. Kim resents their dad because he slept around, was a drunk, and wasn't a good father - plus he cheated on their mom. She thinks they can't afford the nice assisted living place they've put him in, but Amy wants to make it work. Amy later visits Gordon in the home, and he's upset when she tells him Kim threw away a lot of his Mets memorabilia. He's a total curmudgeon.
Amy goes to meet Aaron to set up their interview schedules and meets his best friend, Lebron James. Lebron is insistent on watching Downton Abbey and also getting his parking validated. That night, Amy goes on a date with Steven. He's upset that she's drunk, and their loud conversation gets him into a fight with the other moviegoers. Amy goes outside to smoke a joint, and when she comes back, Steven asks her who all the guys on her phone are. They go outside where Amy admits she sleeps with other guys - Steven is hurt, since he thought they were exclusive. He wants to have a family with her and make her his "CrossFit queen". All Amy can say is that she's too stoned and asks if she can leave. Steven tells her she's not a nice person and leaves, crushed.
Amy gets brunch with Kim, and after Kim doesn't have a mimosa, she realizes she's pregnant. They go to Gordon to tell him, and he's thrilled to have finally a grandchild - which makes Kim angry, since she says Allister is his grandchild. Gordon says Allister isn't really his grandchild, and after he and Amy make fun of the kid together, Kim leaves, furious - she says Amy always takes Gordon's side.
Amy is interviewing Aaron at his sports facility - she's testing out a treadmill body-imaging suit, running when she gets a text from Kim saying she wants to move Gordon to a cheaper facility. Amy asks to slow down the treadmill and starts to have a full panic attack. Aaron coaches her breathing and calms her down, and suggests they get food. They bond over dinner - he compliments her writing, she learns about his family. And after some drinks they get in a cab to leave - Aaron tells the driver two stops, but Amy corrects him: one stop. Aaron's eyes widen. They go to his place and sleep together, and Amy breaks her rule by staying the night.
The next day, Amy tells Nikki about what happened, and Aaron calls to ask if they can see each other again. Amy panics and tells him they'll talk about it at the interview. She and Nikki decide she has to end it. Meanwhile, Lebron is excited for Aaron; he hasn't dated anyone in five years. Amy goes to watch Aaron perform surgery (she pukes while watching) to Uptown Girl, his favorite song, and afterwards tries to politely break things off, but he won't let her. He thinks they like each other and should date - she's dumbfounded - and then Amy gets a phone call that her dad had a fall. Aaron drives her to the home where Aaron stitches up her dad's cut and impresses him with his sports knowledge.
Aaron and Amy begin dating and fall for each other. Both of them are nervous - Amy is worried she's going to screw it up, but Kim tells her she's just finally doing what everyone else does. Lebron coaches Aaron over basketball - he wipes the floor with Aaron until Aaron scores a lucky shot. Amy goes with Aaron to a charity slam dunk contest Lebron is hosting. There are guys doing crazy trampoline dunks, and the Knick City Dancers perform - Amy makes fun of them for being like strippers. Lebron confronts Amy and asks her what her intentions are with Aaron… confused, she assures him they're fine. Later, Amy goes to see Gordon, and disapproves of her relationship with Aaron. She's upset, wondering why he can't support her, and he says he knows she's just like him - she can't have a stable relationship. Amy leaves angry, not talking to her dad for a while.
Aaron goes with Amy to Kim's baby shower - Tom makes a comment to Aaron about how Amy sleeps around that unnerves him. Meanwhile, Amy can't stand the ridiculous hoighty-toighty women and the shower and deliberately grosses them out with tales of her sexcapades. A couple days later, Kim calls her - Amy starts to apologize for the shower when Kim tells her Gordon has died. He was hoarding his meds. At the funeral, Amy gives a speech - she knows Gordon offended everyone - "raise your hand if my dad ever offended you" - but then says she loved him more than anything - "raise your hand if he was also one of your favorite people". After the funeral, she and Kim get into a big fight, Amy says Kim didn't even like Gordon anyway. Aaron tells her he loves her, but Amy can't believe he would pick today of all days to say that. Meanwhile, at work, Dianna tells Amy they're cutting the Aaron story because it was boring.
Aaron is receiving a prestigious award at a Luncheon and brings Amy. She drinks too much and leaves to take a phone call from Dianna during his speech. He finds her smoking pot outside and is upset. They continue arguing at her apartment, and Aaron thinks they shouldn't go to bed angry - so Amy lets him have it, keeping him awake all night ranting and raving… even though the next day is Aaron's big surgery on Amar'e Stoudemire. Aaron shows up completely out of it, and Amar'e panics and cancels the surgery. Aaron goes home and tells Amy that they need to take a break. Hurt, Amy reacts by telling him that they can just break up because the article was canceled anyway. He tells her "you win", and leaves.
Amy returns to her Trainwreck ways and goes out drinking at a bar with her co-workers, including the intern Donald (Ezra Miller). He invites her back to his place, and their bizarre sexual encounter is interrupted when his mom enters, screaming "he's 16!" After nearly committing statutory rape, Dianna fires Amy, but does tell her she was wrong about the article and thinks its quite good.
Aaron is moping all day in his apartment until Lebron calls telling him he's been hurt. Aaron rushes over to find an intervention for him consisting of Lebron, Matthew Broderick, Chris Evert, and Marv Albert. They tell him he's always been afraid of opening up and needs to make things right with Amy, but Aaron insists Amy and him are over.
Amy goes to Kim to mend fences after their fight. After she tells Kim everything that's happened, Kim tells her maybe it's time to change. Amy clears out all the booze from her apartment and goes and pitches her Aaron story at Vanity Fair, who end up publishing it. She sends the article to Aaron and he smiles. He successfully performs the surgery on Amar'e and attends Amar'e's first game post-op. After the game, Aaron is called to the court - where the Knicks City dancers perform… with Amy front and center. She hilariously knows about 80 percent of the moves and can't quite do them exactly the same as the dancers. Included in the songs is "Uptown Girl". For the grand finale, the slam dunk guys come back, and Amy races and jumps off the trampoline to make a dunk…. and immediately face plants. Aaron rushes over to see if she's okay, and she tells him she was trying to show him that she can work hard and try, and she wants to make it work. She finally tells him she loves him, and they kiss, which is shown all over the jumbotron.
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