Following her break-up with Mr. Big, Carrie meets baseball star Joe Starr during a baseball game. Charlotte meets a guy who has an awkward flaw. Miranda is sick of how the girls are always talking about men. Samantha has issues with James in bed.
As Samantha is forced to go to couples' therapy with James, she evades telling the truth about her real problem with him. Carrie tells her friend Susan to leave her abusive husband by accident. Charlotte focuses her effort on getting the perfect dog.
After dating a series of weird guys, Carrie scares off the regular Ben when she tries to find out what he's hiding. Charlotte hooks up with a famous womanizer, but wonders if a strictly physical relationship is enough. Samantha throws a tantrum when she goes for a plastic surgery consultation.
After Carrie's photo-shoot for New York Magazine has been a total disaster, she freaks out when she sees her horrible photo. Charlotte is dating her handyman who is a struggling actor, while Samantha meets the salsa club's co-owner William.
Carrie and Charlotte are surprised when Sam wears colorful clothes at designer Javier's funeral. Charlotte dates a handsome widower, but discovers an unpleasant surprise. Carrie reconnects with Big again. Sam faces an uncomfortable situation, when she ends up having an affair with a married man.
After getting fed up with cheating boyfriends, Charlotte decides to take a break and hang out with the "Power Lesbians." Miranda starts dating a new guy who has a bizarre habit. Samantha dates her gym instructor.
Samantha is in shock when she finds out that she accidentally slept with the same man she previously did 15 years ago. Carrie is upset when Mr. Big starts to neglect her. Charlotte meets the best man during a wedding.
After her date with a married man ends badly, Miranda runs into the bartender Steve who wants to see her again. Carrie wants Big to get to know her friends. Samantha is dating a much older wealthy man with an extravagant lifestyle.
Charlotte is having trouble dating a restaurant critic who has not been circumcised. Miranda and Steve are having a hard time getting together because of their conflicting schedules. Samantha runs into an old boyfriend who had a sex reassignment surgery.
When Samantha starts seeing a real-estate developer, she notices how controlling his female servant is. After Charlotte dates a famous actor, her relationship with him turns out not how she expected. Miranda has an argument with Steve about the financial gap between them.
Samantha attempts to get back at her ex for walking out on her. Charlotte starts dating a pastry chef whom she thinks might be gay. Carrie tries to leave some of her personal stuff at Big's place after she worries that he's not serious about their relationship.
Miranda starts dating a guy who has a weird habit. Carrie is shocked when she finds out that Big is moving to Paris. Charlotte meets a shoe salesman who's obsessed with shoes as much as she. Samantha takes the girls to a new restaurant.
After she goes to therapy to deal with her break-up with Big, Carrie starts dating a fellow patient. Samantha meets a guy who is too obsessed with sports. Miranda faces an embarrassing situation, when she mistakenly thinks that her neighbor is interested in her.
After feeling lonely, Carrie hooks up with her old lover John and tries to bond with him. Things end badly for Charlotte, when she double-dates two men. Miranda feels bad for dating her abusive colleague.
After the wife of Charlotte's brother leaves him, he stays with her, and ends up hooking up with Samantha. When Miranda starts dating a single father, she's annoyed by his son. Carrie keeps dating an author only to hang out with his charming family.
Charlotte tries to seek help with her love life, after her date falls asleep on her. Carrie meets a recovering alcoholic film composer who starts stalking her. Samantha gets an unusual offer from a gay couple.
When the girls go to a party at Hamptons, they struggle with keeping up with the younger girls. Carrie faces an awkward situation when she runs into Big with his 20-something girlfriend. Samantha is mad when her former assistant uses her contact list to throw an upscale a party.
Carrie tries to grapple with the fact that Big got engaged. Miranda gets back together with Steve after their break-up. Charlotte attempts to face her fear of horseback riding. Samantha tries to deal with her new exceptional boyfriend.