Plot
Photographer Will and journalist Jane meet at a wedding in The Hamptons when his extreme tardiness catches her attention. Will approaches Jane at the reception, they chat briefly on the nearby beach, and then Jane proposes they have sex in a closet.
Just as they are about to have sex, Will decides he wants to talk first. Jane storms out and he follows, insisting she not drive drunk. He shares his phone number and she reluctantly gives him hers. Then Will tells her about his most embarrassing sexual encounter and about his first love, who he lost when he paid her a surprise visit and found her cheating on him.
In a diner, Jane then tells her first heartbreak story. Bad boy Michael had attracted her when she was a Catholic school student, introducing her to graffiti and petty theft. One day when he was late picking her up, she went to his home and discovered his father had died. When Jane offered emotional support, Michael broke ties.
Will next talks about Eve, whom he met when she visited his college campus. She convinced him to skip class, they had sex, then she lured him to her NYC apartment. Soon he was skipping classes and spending most of his time with Eve. One day, when Will warned he wouldn't be able to visit for a month due to exams, Eve declared that she was in love with him. He then did an Irish exit.
Jane, in turn, tells Will about Elton, a man who charmingly bought her a drink in a bar while she was underage. Elton had displayed a lot of eccentricity but she hadn't realized he was mentally ill until one evening when he shouted his feelings for her from the edge of a rooftop. Jane visited Elton in the institution where he was placed, but ended the relationship because of his instability.
Jane admits that she recently broke off an engagement with a lawyer and asks Will if he currently has any significant relationships. He assures her that although he's had flings in the past, he's been single for the past year.
Jane's most heartbreaking relationship story happened when, as a grad student, she got involved with a professor who was agoraphobic and a recovering alcoholic. She soon moved in with him and accepted his non-existent social life. After months together, they tried to attend a party but he backed out at the last moment; upon returning home later, she found him drunk on the porch. In the morning, desperate to not lose her, he proposed, but she decided to leave him. When Will asks whether she's seen the professor since, she is shown visiting his grave in a flashback and she admits she feels responsible for his death.
Will starts to tell Jane about the singer Audrey but doesn't finish the story as they passionately make love in his motel room. When they finish, Will goes to the bathroom and Jane sees a card in his bag on which he has written "I love you, I love you, I love you." Will explains that he and Audrey had gotten serious and moved in together, but he soon broke up with her and at that time Audrey revealed she was pregnant. The card is for their almost five-year-old daughter, Juliet.
Jane, upset that Will didn't tell her about this "significant relationship", abruptly gets dressed to leave. Will begs her to stay but she insists he is incapable of commitment. While a distraught Will drives to a beach, phones Juliet, and then jumps into the ocean, Jane walks along the highway and calls a Lyft. Emotionally torn, she asks the driver to pull over. Just as she is about to go back, Will drives by, so they follow him.
They end up at a beach where they'd talked before and he excitedly tells her all about Juliet, showing he adores her. They both admit that as they've talked, they've become increasingly interested in each other and motivated to share more. They promise to take a leap of faith to be together, and seal it with a kiss. [2]
