San Fernando Valley, 1973 – Several boys are getting ready to have their pictures taken, while a couple of others set off a cherry bomb in the bathroom. One of the boys, Gary Valentine (Cooper Hoffman), sees the photographer’s assistant, Alana Kane (Alana Haim), and becomes smitten with her. He tries to talk to her, though she seems disinterested due to the fact that she is 25 and he is 15. Gary tells Alana that he is an actor, and he eventually succeeds in getting her to agree to hang out with him, but not as a date.

Gary and Alana meet at a restaurant that he frequents since he appears to know the manager. The two discuss their jobs, and Gary mentions that he also works with his mother at a public relations company. Gary assures Alana that they are not going to forget each other. They walk home, and we see Alana lives with her parents and two sisters (all played by Haim’s real family), while Gary lives with his brother Greg (Milo Herschlag).

Gary works with his mom, Momma Anita (Mary Elizabeth Ellis), and they meet with a restaurant owner, Jerry Frick (John Michael Higgins), and his wife Mioko (Yumi Mizui), over a new Japanese restaurant they are trying to open. Jerry speaks with a cringey racist accent to his wife. Later on, Anita tells Gary that she can’t chaperone him for a trip to New York where he will be featured on auditions and a variety show.

Alana accompanies Gary to New York, where he rejoins his castmates from the film “Under One Roof”, where he starred as one of many siblings along with renowned actress Lucille Dolittle (Christine Ebersole). During the show, Gary hits Lucille over the head with a pillow, and when being interviewed, he makes a joke about “doing three beavers”. Lucille later angrily chastises him and hits him. Afterward, Gary meets with an agent, Gale (Maya Rudolph), and does a commercial for a vest. While this happens, Alana befriends another actor named Lance (Skyler Gisondo).

Upon returning to California, Alana begins a relationship with Lance. However, when she brings him over for dinner with her family, he declines to say a prayer because, despite being raised in the Jewish faith, he identifies as an atheist. Alana breaks things off with him shortly afterward.

Gary soon gets into the waterbed business and gets his friends Kirk (Will Arangola) and Mark (Griff Giacchino), along with Alana, now that they are becoming friends, although Gary is still in love with her. They go to an expo called Soggy Bottom, where there are other booths like one for “The Munsters”, with Fred Gwynne (John C. Reilly) in attendance. As Gary tries to sell the water beds, cops come to aggressively arrest him on suspicion of murder. Alana runs all the way to the police station, where Gary is soon let go when their first suspect says he doesn’t know Gary. He leaves the station and hugs Alana.

Alana operates the phones at the waterbed business, with Gary telling her to sound “sexier”, but he feels she overdoes it. He later accompanies her to meet an agent, Mary Grady (Harriet Sansom Harris). When she asks Alana if she would do nudity in films, she initially says yes, but Gary urges her to say no. The two argue on the way home because Gary isn’t comfortable with audiences seeing Alana nude when he can’t. She later relents and shows him her breasts but slaps him when he asks to touch them.

Alana joins Gary at an event to sell waterbeds, where Gary meets a girl from school named Sue Pomerantz (Isabelle Kusman). The two chat and go off to hook up, which Alana sees and appears jealous for it. She randomly kisses another guy out of spite and then walks home in nothing but her underwear (as she was modeling that way).

Later on, Alana goes to an audition for a part alongside actor Jack Holden (Sean Penn). He takes a liking to her and compares her to Grace Kelly. Jack takes Alana to a bar, “The Tail o’ the Cock”, where Gary and his friends also make an appearance. Jack runs into his old friend, director Rex Blau (Tom Waits), and they convince everyone in attendance to watch Jack recreate a motorcycle stunt from his film “The Bridges of Toko-San”, which he did with Kelly. Alana sits on the back of the motorcycle, but as soon as Jack takes off, Alana falls backwards. Gary runs all the way to Alana to make sure she is okay while everyone else cheers for Jack. He walks back with her to the waterbed store where she falls asleep. Gary contemplates groping her but decides against it.

News reports come out that there is an oil embargo that is creating a gas crisis, which Alana says is in part thanks to the waterbeds, since they are made from vinyl, and vinyl is made from oil. The two, plus Greg, Kirk, and Mark, later deliver a waterbed to the home of producer Jon Peters (Bradley Cooper), who is something of a lunatic. He grills Gary for the pronunciation of his girlfriend’s name (being Barbra Streisand), and explicitly threatens to kill Gary’s whole family if he messes anything up during the setup. Gary and Alana set up the water bed, but accidentally pull the hose out and get the carpet wet. They get the other three boys out of there quickly.

On their way out, they run into Jon coming up a hill, where he forces them to take him to the gas station to fill up since his car broke down. They leave him there when they see Jon threatening to light a man on fire by spraying him with the gas nozzle while holding a lighter. They drive back towards Jon’s car, where Gary starts to smash the windshield. Unfortunately, their truck runs out of gas, and they have to roll the truck carefully down the hills backwards until it eventually stops in the middle of the street somewhere. Gary and the boys go off to get gas, while Alana sits on the street. Jon walks nearby and throws a garbage bin through a store window, but she manages to avoid being seen by him before he tries to hit on two tennis players.

With the waterbed business failing from the gas crisis, Gary and Alana look to move onto other work. Gary invests in a pinball arcade while Alana decides to do volunteer work for mayoral candidate Councilman Joel Wachs (Benny Safdie). Gary and Alana have an argument, leading to them parting ways.

While Alana is taking calls at the campaign office, she notices a creepy guy (Jon Beavers) scoping the office out. She confronts him but he gives her vague responses as to why he is there. Alana is later invited to drinks with Wachs, where the creepy guy is sitting nearby again. She meets Wachs’ partner Matthew (Joseph Cross), and Alana learns that Wachs is gay and that the creep is most likely a spy trying to dig up dirt on Wachs and his campaign. Wachs asks Alana to go home with Matthew and pretend that she is his girlfriend. When they get home, Matthew breaks down in tears, asking Alana if she has a boyfriend. She says “yes and no”, but they both cry over the fact that the guys in their life are jerks.

Gary is at the opening of his pinball arcade, dealing with obnoxious kids and adults. He runs into Alana’s friend and asks where she is. He runs to the campaign office to look for her but she is not there. Similarly, Alana goes to the restaurant where she first went out with Gary, but he isn’t there. They eventually keep going until they literally run into each other in front of the movie theater. Gary brings Alana back to the arcade and introduces her as “Mrs. Alana Valentine”. She calls him an idiot, but he then kisses her.

The two run off again together, with Alana telling Gary that she loves him.

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In 1970's California, 15-year-old actor Gary Valentine falls for 25-year-old photographer's assistant Alana Kane. Although she doesn't reciprocate his feelings, she forms a friendship with him as they go through several misadventures, such as going into the waterbed business and dealing with people like egotistical actor Jack Holden and insane producer Jon Peters.

After the waterbed business goes under due to a gas crisis, Gary moves onto opening a pinball arcade while Alana works as a volunteer for the campaign of mayoral candidate Councilman Joel Wachs. Gary and Alana have an argument that leads to them parting ways, but by now, Alana has begun to acknowledge her feelings for Gary. After having drinks with Wachs, Alana learns he is gay and wants her to be the beard for his partner.

Gary and Alana eventually realize they miss each other and find their way back to each other, and they share a kiss.