In Montauk, New York, Maddie rushes out of her house when she sees her ex Gary use his tow truck
to take away her car. It turns out the vehicle is getting repossessed because she owes property
taxes on the home she inherited from her mother, and her sources of incoming are only bartending
and Uber driving. Without the car, there are even fewer chances of paying that debt. Gary is
mad at Maddie because she ghosted him, but Maddie still tries to flirt with him and says she’s been
thinking about him all this time. At first Gary seems to believe her, but then Maddie’s late-night
guest comes out of the house too. Maddie tries to pretend he’s a cousin, but the guy begins getting
affectionate, so Gary leaves with the car. Now Maddie has no choice but to rollerblade to work.
On her way there, she sees Gary’s tow truck parked nearby while Gary is inside a store getting food.
She immediately uses the chance to unfasten her car from the truck and tries to drive away,
but she forgets about the extra hook and now she’s stuck there for Gary to see. When he comes out,
he lifts the hook and calls the police. Moments later, Maddie is bailed out by a friend and rushes
to work. At the bar, a guy tries to ask for a drink minutes before they’re properly open,
so Maddie ends up arguing with him to the point where the manager scolds her and sends her to
do something else. While folding napkins, Maddie rants about her situation to her pregnant friend
Sara and her husband Jim. At that moment, Sara finds an unusual Craigslist post: two helicopter
parents are looking for a woman in her early 20s to date their introverted 19-year-old son
for the whole summer, and the payment would be a Buick Regal car. Maddie decides to apply even if
she's older. The next day, Maddie rollerblades to the family’s house, which takes extra effort
because she has to make her way up an elevated road and a set of stairs. The Beckers ask some
basic questions, and when they learn that Maddie is 32, they hesitate to hire her. However Maddie
quickly makes up a speech, saying that if the ad was still up is because all the other young girls
failed them, so what they need is someone mature enough that will help their son gain experience in
dating and guide him to become a proper man. The Beckers like the idea and explain the situation:
their son Percy is a 19-year-old introvert, the socially shy kind that doesn’t talk to
anyone unless it’s online. He doesn’t drink, doesn’t smoke, and doesn’t go to parties. The
parents are worried that he is missing out on the teenage experience, and they want him to have fun,
learn how to date, and build up his confidence before he goes off to Princeton. Maddie gets
the job, but before she leaves the parents tell her that Percy mustn’t know the truth,
she must keep it natural to make him feel better about himself. After borrowing Jim’s old van,
Maddie puts on a seductive dress and shows up at the animal shelter Percy volunteers at,
where she specifically asks for his help while she pretends she wants to adopt a dog. Percy shows her
a dog named Milo while Maddie keeps flirting and throwing lots of innuendo to no avail. Then they
go to the office to fill out her application and Maddie has to drag a small couch to the desk to
keep on flirting, but the couch is too low and she doesn’t cause a good impression. She keeps
on flirting while Percy asks her questions, which makes him uncomfortable. He decides to end the
interview quickly, but Maddie needs an excuse to keep on talking to him and offers him a ride home
because she knows his address. When Percy wonders how she knows that, Maddie saves her mistake by
saying it’s on his bag. At that moment Percy’s coworker Crispin comes to see what’s going on,
and Percy takes the chance to say he’s leaving early. Maddie follows him outside and finds him
grabbing his bicycle, so she offers to give him a ride again and puts the bicycle in the back of the
van to prove he can’t say no. Once they’re on the road, Maddie tries her best to carry on a proper
conversation and makes a joke about Percy being her hostage. Between this and the creepy things in
the back of the ban, Percy is getting a little scared. When Maddie takes a different route,
Percy tries to ask for help with his phone but Maddie takes it from him. Moments later,
they arrive at Maddie’s home and Percy assumes she’s kidnapped him for real so he throws paper
spray at her eyes. Crying out in pain, Maddie explains she just thinks he’s really hot and that
she had been trying to score with him. Percy can’t believe it but he apologizes as he helps wash her
eyes with a hose before they agree to meet again tomorrow for a proper date. The following evening,
Maddie is waiting at a bar and sees Percy arrive wearing a suit with short pants
because of the hot weather. The waitress asks for their order and Percy tries to get a soda,
but Maddie changes it for a cocktail so he can learn to live a little. When their drinks arrive,
Percy spits it out as soon as he takes a sip, and Maddie has to force him to drink more so
he can learn to handle alcohol before college. She tries to keep up conversation again, but
Percy is always shy and awkward. Suddenly they’re uninterrupted by one of Maddie’s ex-boyfriends,
who brags about being married now and mocks Maddie for ghosting him, however Maddie insults him with
some good burns until he leaves. Afterward, Maddie and Percy go for a walk on the beach. Maddie asks
Percy to go skinny dipping with him, but Percy refuses and an argument ensues. To distract him,
Maddie starts undressing slowly to let him take a good look before she jumps into the
water. Not wanting to be left behind, Percy soon joins her, and Maddie wraps her arms around him
to try to get him in the mood. Suddenly a group of drunk teenagers appear on the beach and make
fun of them before stealing their clothes. Maddie yells at them, and when the teens don’t listen,
she comes out of the water naked to throw sand at their faces and start beating them up. The teens
defend themselves and Maddie gets kicked in her delicate area but she recovers quickly and body
slams a guy, scaring the group into leaving. Then Maddie goes back to Percy, but he disapproves of
Maddie’s use of violence, which angers Maddie as she points out that it was self-defense and
that Percy needs to learn how to stand up for himself. She also tries to get busy with him,
but Percy explains he can’t do it with strangers. He needs to have a connection first, especially
for his first time. Annoyed and frustrated, Maddie leaves the water and dresses up before getting in
the car, bringing Percy’s things with her. A naked Percy follows her and demands to have his clothes
and phone back, but Maddie only gives him his clothes before starting to back off. Desperate, a
naked Percy jumps on the hood of her car and keeps asking for his phone, but Maddie doesn’t care and
begins driving with Percy still on the hood. When they make it to the road, their shenanigans get
the attention of the cops, and Maddie worries about potentially losing her license. In order
to lose the police, she dangerously drives past the incoming train. Afterward, the duo goes to
Maddie’s house, where she begins a dance for Percy. When Maddie asks Percy to hit her rear,
he doesn’t know how and ends up kicking her. Next vMaddie tries to dance on his lap, but
Percy complains about the weight on his thigh so Maddie switches their positions, moving him like a
baby on her lap instead. Then Maddie asks again if he wants to get down to business, and when Percy
begins explaining he wants to but he’s too nervous because of his lack of experience, he suddenly
begins feeling itchy. Maddie raises his shirt and discovers he’s got a rash caused by his anxiety,
but she doesn’t judge, she immediately grabs some cream and helps him out. Feeling comforted,
Percy opens up about how he dislikes being socially awkward because he’s never made
friends unless it’s online or his former nanny. Maddie returns the favor and tells him how she’s
lived in this house her whole life to take care of her sick mom. Her dad wasn’t around because he had
a family in the city and her mother had only been a fling. After sharing such a sweet moment, they
agree to start dating before getting intimate. The next few days, Maddie and Percy begin
spending lots of time together: they walk Milo and other dogs from the shelter, play laser tag,
and win lots of things at the arcade, where they tease a kid until they get kicked out. They have
lots of fun together, and Percy starts becoming more comfortable around Maddie. At the arcade,
he spent his tickets on a beer hat for her and also gets a finger trap that he tricks her into
using with him. Maddie freaks out, but Percy is patient and teaches him how to get out of
it. They start chatting and they learn more about each other, like the fact neither of them went to
their proms. Maddie also tells him that she once wrote to her dad to ask why he wouldn’t visit her,
but the letter returned unopened. Having this vulnerable moment allows Percy to gather courage
and finally kiss Maddie. Afterward they go for a walk and bump into Percy’s former nanny Jody,
who turns out to be a middle-aged guy. Jody notices they won a frisbee at the arcade
and throws it for Percy to go pick it up. Once Percy is far from them, Jody asks what Maddie’s
intentions are with Percy, accusing her of wanting the family's money. Maddie says she only wants
to date Percy and shuts Jody up by implying he wants the same thing. When Percy returns,
Jody and Maddie just pretend to get along for his sake. Sometime later, Maddie hears someone ring
the bell at her house and finds a man she doesn’t recognize. It turns out they went to school
together, and the guy acts as if they were super close, but Maddie barely remembers him. Soon the
truth comes out: the guy is there for the house, but Maddie still refuses to give it up and kicks
the guy out, ignoring his legal threats. Later that night, Percy picks Maddie up in a limousine
so they could go to a fancy dinner they’ve planned as a way to have their own prom. In the car,
they even exchange flowers. Once they make it to the restaurant, they have a good time chatting and
laughing. Percy shares that he didn’t want anyone at school to notice him because if they didn’t
notice him, then they couldn’t make fun of him, so Maddie comforts him by saying that they should
see how great he really is. Then Maddie notices a piano and convinces a very nervous Percy to
play it. He turns out to be quite good and he signs along to his playing, choosing “She's a
maneater” by Hall and Oats as a tribute to Maddie. The people in the restaurant love it and everyone
claps while he returns to the table, where Maddie can’t stop telling him how talented he is. Their
chat is suddenly interrupted by Natalie, a family acquaintance that will also attend Princeton.
Natalie and Percy start chatting very casually and Maddie immediately gets jealous, often trying to
get Natalie to leave. It doesn’t work and Natalie invites Percy to a party for future Princeton
students. Maddie tries to say no, but Percy tells her he’ll keep it in mind. After Natalie leaves,
Percy brings up the subject of his college plans and how they could see each other on the weekends,
but Maddie explains she doesn’t do long distance. For her this is a summer fling that will end when
Percy leaves. Hurt, Percy storms out and Maddie immediately follows him into the limousine,
but they awkwardly sit very far from each other and Percy begins getting drunk, which is a first
for him. Suddenly Maddie notices they’re going in a weird direction and Percy explains they’re
going to Natalie’s party. It was Maddie who told him to hang out with school friends more,
so if she doesn’t want to attend, she shouldn’t come. The limousine stops and Percy rushes into
the party, dropping his flower in the way. After some hesitation, Maddie follows him inside only
to lose him in the crowd. Maddie starts asking around for Percy, but all the youngsters judge
her for being a grown woman trying to fit in with the teens and whenever she responds rudely,
they threaten with recording her for social media. Eventually two girls inform her that Percy went to
a room with Natalie. Worried that Percy may be having his first time with someone else,
Maddie rushes upstairs and begins checking every room, getting disappointed that the new generation
wasn’t doing the dirty. At last she finds a locked room and since nobody answers when she knocks, she
runs and throws her full body against the door to break it down. Natalie and Percy are together and
half-undressed, but Natalie swears that nothing happened because Percy is drunk, he also confesses
he took something. Maddie immediately takes Percy to the bathroom and forces him to throw up
everything, but it turns out he only took medicine for his hangover, not anything illegal. At that
moment the party host arrives with his parents, who begin arguing with Maddie because she’s an
adult in a teen party. Percy won’t let anyone insult Maddie and tries to punch the father,
but the guy dodges and he ends up punching Maddie on the neck instead. The couple leaves the party,
and in the limo, Percy lies his head on Maddie’s lap so she can comfort him while he apologizes for
accidentally hitting her. Then he admits he’s ready for her and takes out some protection,
but while Maddie teaches him to open it, he suddenly confesses he loves her. Maddie feels
uncomfortable and points out that Percy is drunk so they shouldn’t do anything tonight,
Percy can see her point and goes back to resting his head on her lap for the rest of the ride. The
next day, Percy wakes up in such a good mood that his parents can’t help commenting on it.
Percy says he finally wants to get his own driving license so he can drive his girlfriend around, and
his parents are incredibly happy to see him coming out of his shell. However the happiness instantly
disappears when Percy tells them he isn’t going to Princeton because he wants to stay in Montauk with
Maddie. The Beckers tell Percy to wait for them in the car, and once he’s gone, they call Maddie,
who informs them that she wants to cancel the deal because Percy is getting too attached. The parents
agree and tell her that she still gets the car because she did bring Percy out of his shell,
but the last thing she needs to do before breaking up is to convince him to go to Princeton. While
Maddie accepts, Percy is fooling around with the technology in the car and accidentally connects to
the phone, which causes him to hear the last bit of the conversation and his heart breaks
by learning Maddie had only been paid to be with him. After thinking about it, Percy invites Maddie
to lunch without his parents’ knowledge, and the Beckers are shocked when Maddie shows up at their
door. During the meal, Percy tries to make his parents and Maddie have a conversation, pushing
for questions that will reveal their secret, but Maddie and the Beckers try their best to play
along. Suddenly Percy gets a call and goes outside to meet with Crispin, who helps him destroy the
Buick. It’s a very sturdy car though and not even hitting it with a rock works, so Percy
drives it into the forest to crash it against a tree. Then the tree falls on top of the car,
finishing the job. When he returns to the house, Percy goes straight to his room, so Maddie follows
him to check on him. Percy tries to kiss her but Maddie rejects him with the excuse his parents
could hear them, so instead he tries to get the truth out of her. Maddie continues to lie and
to distract him from the subject, she agrees to get frisky with him, only for Percy to be done
in seconds. Afterward Percy admits he knows about Maddie’s deal with his parents. Maddie apologizes
and says it was real for her, but when he ignores her pleas, Maddie gets angry. She points out he’ll
never understand what poor people have to do to survive, but Percy responds by saying she’s
wasting her life in that house waiting for her dad to apologize, causing her to leave very upset.
Sometime later, Percy confronts his parents and asks them to stop doing everything for him and to
let him fail or succeed on his own. The breakup is hard on him though and he goes back to being
an introvert that stays in his room playing videogames. Meanwhile Maddie still receives
the damaged car, which she begins using for her Uber driving job. Clients are often wary when they
see her arrive, but she forces them into the car anyway. By working hard in the bar and driving,
Maddie eventually saves enough money to pay her debts. She goes out to celebrate with Sara
and Jim, who have big news: they are moving to Florida because they can’t afford to buy their own
place in Montauk. Maddie is shocked that they’re leaving, but Sara tells her that she’s even more
shocked that Maddie is staying despite how unhappy she seems to be here. To prove she’s actually
doing well, Maddie takes a guy home, but she suddenly finds herself trying to know him better
instead of getting frisky with him because she wants a connection. The guy finds Percy’s finger
trap and tricks Maddie into using it, but instead of his finger, he uses his banana, so Maddie kicks
him out. The next morning, Maddie finds the letter and realizes that she needs to move on. She burns
the letter, fixes the car, apologizes to Gary with a hug, and then decides to sell her house
but with a catch. She also wants to apologize to Percy, but he won’t answer her messages so
Maddie begins looking for him everywhere. Jody and Crispin are mad at her and won’t help her,
but Percy’s parents tell her he’ll be at the Princeton mixer. Maddie goes there and apologizes
as she explains their friendship was real, but when Percy ignores her and tries to leave, Maddie
jumps on top of his car’s hood. Taking inspiration from her past shenanigans, Percy begins driving
around with Maddie still on the hood, hitting lots of things on the way and accidentally setting
Maddie’s jacket on fire. Panicking, Percy drives the vehicle into the sea to put out the flames
and gets out of the car to help her. Maddie takes the chance to apologize to Percy, who cries as he
forgives her. The duo stays on the beach and talks about their plans for the future: Percy is going
to Princeton after all, and Maddie will be moving to California. Then they agree to stay friends.
Sometime later, Maddie finally sells her house but in a way that is going to Sara and Jim so
they don’t have to move and can raise their child here. Percy says goodbye to his parents and leaves
the house to find Maddie offering him a ride to Princeton on her way to California. She also
reveals that she’s adopted Milo, and the three of them get together in the car to start a new life.