No Hard Feelings - Date him hard

Maddie, a woman in her 30s, works as an Uber driver in Montauk. Despite living in a house inherited from her mother, she is far from wealthy and desperately needs money to pay her bills. One day, she stumbles upon an unusual job ad on Craigslist: a wealthy couple is offering a car in exchange for someone to have sex with their son. Though skeptical, Maddie's need for a reliable vehicle for her Uber business compels her to attend the interview.

The couple, who live in a luxurious home, explain that they want their shy son, Percy, to experience love and sex before he leaves for college. While Maddie is older than they initially envisioned, her understanding of their requirements and confidence in her ability to help Percy overcome his shyness secures her the job.

To meet Percy, Maddie is instructed to find him at an animal shelter where he volunteers. Dressed seductively, Maddie attempts to flirt with Percy, but he is shy and busy in assisting her with adopting a dog. When Maddie offers Percy a ride after his shift, he mistakes her for a kidnapper and pepper sprays her upon exiting the car. After realizing Maddie's harmless intentions, Percy asks her out on a date the following day.

Percy, dressed to impress, meets Maddie at a bar. He tries alcohol for the first time, but finds it unappealing. Maddie then takes him to the beach and convinces him to go skinny dipping. Their fun is interrupted when a group of strangers steals their clothes. Maddie emerges from the water and confronts the thieves, beating them up. Percy, believing Maddie overreacted, so Maddie takes away his clothes and leaves. He chases after her and jumps on her car in an attempt to retrieve his belongings. They manage to evade the police and end up back at Maddie's house. Maddie tries to seduce Percy, but he develops a rash due to anxiety.

Despite this awkward start, they continue to date. Percy, who has never attended prom, suggests they go together. At a fancy restaurant, Maddie encourages Percy to play the piano for the crowd, something he would never have considered before meeting her. Later, Percy runs into a schoolmate and is invited to a party. During dinner with Maddie, they discuss their future plans. Maddie expresses doubts about long-distance relationships, while Percy believes they can work. They argue, and Percy leaves to attend the other party. Maddie later goes to the party to find him.

Percy realizes he is in love with Maddie and decides he wants to stay in Montauk instead of attending Princeton University. His parents are shocked and immediately contact Maddie, offering her the car if she can convince Percy to go to college. Percy overhears their conversation and is furious at being manipulated. Seeking revenge, he tricks Maddie and his parents into having a meal together, then crashes her car. Eventually, they reconcile. Percy goes to Princeton, and Maddie sells her house to start a new life.

Motivated by the promise of a new car, Maddie initially agreed to help Percy come out of his shell. In the end, she gains more than she expected. She learns to let go of the past and embrace a fresh start. Percy also experiences significant growth. He begins to act like a typical teenager, becoming less shy.