It's autumn in New York and Carrie's yearning for some company. She invites herself over to Big's apartment, finding it filled with shipping boxes. Big tells her that he's moving to Napa, California where he bought a vineyard. Dazed and confused, Carrie joins him in a glass of wine and a slow dance to Big's parents' favorite song, "Moon River." Samantha is also feeling abandoned as Richard is late for their rendezvous. Although she's suspicious of his excuses, she gives him a token of love: a framed picture of hearts.

At the girls' next get-together, Carrie breaks the news about Big's impending departure and wonders if she should sleep with him one last time. Samantha tells the girls that she's a 'love-a-holic' and is worried as she's sure relationships never work. Carrie starts thinking about fate and wonders: Can you make a mistake and miss your fate?

Meanwhile, while leading a tour at the Museum of Modern Art, Charlotte is asked out by one of the visitors. At first she's resistant but when she spots Trey and Bunny wandering through the museum, she says yes to the potential date, Eric.

Samantha is increasingly concerned about her 'relationship' as Richard isn't reacting to her sexual advances. She asks him if he's sleeping with another woman and he denies it. She decides to spy on him.

Charlotte's date with Eric is going well. Both recent divorcees, they seem to have a lot in common. However, when he sees her luxurious Park Avenue abode, he goes on a rampage about her being a 'rich girl.' She shows him the door and gets rid of him quick.

Carrie gets all glammed up for her last night with Big. In a carriage ride through Central Park, Big tells her he'll miss her very much. They start to kiss but are interrupted by a call from Miranda who's in labor. The horses pick up their gait and Carrie dismounts at the hospital. Big gives her his classic wink goodbye.

Carrie keeps Miranda sane as she gives birth to a healthy baby boy. Miranda tells an exuberant Steve that she wants to name their child, Brady, Brady Hobbes. Samantha's in a different kind of labor of love as she follows Richard incognito in a wig and dark glasses. She catches him in bed with another woman and proceeds to smash the heart painting she had given him.

Carrie rushes off to try to catch Big before his plane takes off, but it's too late. In the apartment she finds the 'Moon River' record with a note reading "If you ever feel lonely" and a plane ticket to Napa with a note reading, "If I ever feel lonely."