10-year-old Chip takes a swim in his grandparents’ pond while the family gathers in the great house. He thinks about the dark water and the swimming newts until his sister Elizabeth, or Libby, comes down to find him. They return to the house for the Fourth of July dinner, joining their grandfather Charles, or Bear, their grandmother Slim, mother Julia, aunt Diana, and uncle Charley. They nurse their drinks, waiting for Uncle Flip to arrive. Disgusted by his tardiness, Slim urges Bear to begin.

As Bear launches into a toast, Julia clutches Chip to her body, nestling her face into his neck. Then an inebriated Flip shows up with a woman he met at the local pizzeria, Pearl Spang. Visible facial expressions pass between the family members. Slim makes remarks under her breath about Pearl and about Flip’s tardiness, appearance, and disrespect.

Bear launches back into his speech, announcing that he will be passing the family banking business over to Charley. An angry Flip lashes out, accusing Bear of denying him and Julia their due and favoring Charley just because he was named after Bear. Pearl eats unabashedly, seemingly unfazed by the drama. When Bear and Slim attack Flip for being gay, Libby lashes out, too, inspiring a scolding from her grandparents. Finally, Libby, Julia, and Chip leave. In the car, Libby and Julia agree they hate the family.

Years pass, and things change for Chip’s family. Julia leaves the family business and starts her own firm. Libby goes to school and does well. She gets to know Flip, who takes her under his wing. Libby ends up working summers on Martha’s Vineyard, where she invites an adolescent Chip to join her. He gets to know her friends, attends parties, and enjoys himself.

As the years pass, Chip struggles his way through school. He has a low GPA and does poorly on the SATs, but his grandparents’ generous donation to a renowned college guarantees him admission. Around this time, Charley and Bear offer him a job. Having no alternate plans, a flattered Chip accepts the offer.

Chip works for the business for the next few years. He doesn’t invest himself, but coasts along, drinking every night with his coworkers. He tells himself he has no other choice outside this life. One such night, Chip brings a girl home and is so drunk he doesn’t remember what happens between them. The girl brings charges against Chip, but his grandparents have them dropped.

Time passes, and Chip continues on this way. Then one day, Charley and Bear call him into the office. Chip thinks he is finally getting a promotion, but they let him go—insisting they’ll always take care of him because he is family, but that he’s not the right fit for his current position.

A devastated Chip contacts Libby, suggesting they go out for drinks. Libby explains that she no longer drinks given their family’s history of alcohol dependency. Chip dismisses her, sure he doesn’t have a dependency. However, he spends the next several days holed up in his house, drinking alone. When Libby comes over, she insists on helping him. She gets him out of the house and sets him up at the caretaker’s cottage on their grandparents’ summer property, where they rarely stay nowadays. She bought him a new bed and urges him to take as long as he needs to get sober and start over. She promises they’ll all reconvene there for Thanksgiving.

Chip spends the following days settling into the cottage, unsure what to do with himself. Then one day, he takes a walk and runs into a woman and her dog in the woods. While chatting, he realizes she is Pearl Spang. He pretends to be the hired caretaker and agrees to stop by Pearl’s restaurant in town.

One night, Chip borrows some of Bear’s old clothes and goes to the restaurant where he sees Pearl. Afterwards, he follows her car home (per her instructions), and they drink wine and have sex. Chip is overwhelmed by the experience, because Pearl’s name is a slur in his family and this is the first time he’s had sex sober. In the morning, however, he feels pleasant eating breakfast with Pearl. Sensing his attachment, Pearl insists they are not dating and sends him home.

An offended Chip returns to the cottage, disgusted that someone like Pearl would reject him. Over the following days, he channels his anger into redoing the cottage and boathouse, stripping shingles and paint and redoing the spaces.

Then one day, Pearl shows up on the property to apologize. She suggests they continue a sexual relationship with no strings, asserting that Chip doesn’t want her as his girlfriend anyway. A relaxed Chip feels silly for having gotten angry.

The two continue their affair over the following weeks. Chip finds himself enjoying life. He is proud of the cottage and boathouse and loves spending time with Pearl. He likes being in her space, too, and marvels at its tidy beauty.

Just before Thanksgiving, Libby calls to say they won’t be celebrating the holiday there after all. A despondent Chip heads over to the restaurant and goes home with Pearl, to whom he vents about his disappointed holiday plans. Shocked, Pearl reminds him they aren’t dating and insists she can’t invite him to spend the holiday with her family of protective brothers. In the morning, she tells Chip they should take a break, asking for a week apart.

Over the following week, Chip misses Pearl immensely. He realizes his feelings for her and starts imagining their future together. At the end of the week, he goes to the restaurant, where he is horrified to see another man’s car following Pearl home. He follows them back to the house, and watches through the window as they kiss. Stewing over his hurt feelings, Chip takes a long drive to cool off. He ends up at a jeweler’s, where he buys Pearl a sapphire bracelet. Then he buys a handle of bourbon, which he opens before returning home.

Chip returns to town, drives to Pearl’s, and lets himself in with her spare key. He decides to lie on her bed and wait for her, surprising her when she returns from work. Realizing she might be upset to see him on her bed, Chip hides in the closet with the bourbon. When he hears the door, he is horrified to discover that Pearl has brought a man home. Chip stays in the closet while they are having sex, slipping out after they fall asleep, grabbing the bracelet out of the dark hall, and driving home without the headlights.

Back at home, Chip realizes he urinated in his pants and left the bourbon in Pearl’s closet. Terrified of the repercussions, he calls Libby in a panic. He doesn’t reveal the truth, but she deduces he is in trouble. She promises to be there the next day, urging him to take a shower or walk to calm down. Instead, Chip holes up in Bear’s study in the great house, drinking excessive amounts of expensive liquor. Pearl’s horde of angry brothers arrives, yelling and breaking into the cottage.

After they leave, Chip finds the cottage in disarray and a threatening note from the brothers. He paces around the cottage until returning to the great house for more liquor. Finally, he decides to return to Pearl’s with the bracelet. He takes his gun and heads out. In the trees next to her house, he can see Pearl inside alone.

When Pearl discovered the bourbon, she knew Chip had been stalking her and contacted her brothers. She felt sorry for him, a rich boy pretending to be someone he wasn’t. At home alone, she lights a fire and sits on the couch, enjoying the warmth and thinking nothing of Chip. Although she relies on her brothers to protect her and enjoys having sex with men, the time she spends alone is most important to her.

Meanwhile, Chip is overcome by despair witnessing Pearl’s contentment without him. He shoots himself with the rifle, dying by suicide.