Carrie has a hot date with Jack but worries the entire time that she'll screw it up. To calm down, the girls suggest that she has a "sim-u-date" prior to her date with Jack. Though the "sim-u-date" doesn't go well and Carrie runs into Aiden, she decides to still go on her date with Jack. Meanwhile, Charlotte is still in love with Harry, and Harry still refuses to marry a non-Jew. Miranda admits her feelings for Steve, but is crushed when she finds out that he's in a relationship. Samantha sleeps with her new stockbroker neighbor and he gives her stock tips.
Carrie and Jack continue to have the perfect relationship until they realize that they don't have the same passion for each other in bed. Meanwhile, Samantha pursues a waiter at a raw foods restaurant, Miranda uses TiVo to fill the void left by Steve, and Charlotte announces she's converting in order to be with Harry.
Carrie visits Berger's apartment for the first time and discovers his "ex-file". Meanwhile, Charlotte sacrifices pieces of her past as the day of her official conversion to Judaism approaches; a diaper bag-discovery forces Miranda to deal with the reality of Steve's new relationship; and in a bit of role-reversal, Samantha "waits" on Jerry the waiter.
Carrie brings Berger out for a dinner with the girls, and the conversation flows smoothly, but things come to a screeching halt when Berger gives Miranda some blunt advice about her lovelife. The advice may be difficult to hear, but ultimately, Berger scores points with the girls for his honesty. Later that night, Carrie and Berger share their first "I Love Yous", and things couldn't seem to get any better.
After taking Berger out on a date to celebrate the success of her book, Carrie's success makes Berger feel like she's rubbing her success in his face. Samantha continues to date Jerry and tries to help him become big in New York, first by changing his name. Charlotte is still down about being dumped by Harry, and Miranda tries to get closer to Steve.
Carrie gets called for jury duty and is unable to get out of it. Later, she and Berger decide to take a one week break from each other. Miranda begins to feel the pressures of being a single mother when Brady sees Magda as more of a mother figure than Miranda. Meanwhile, people at the synagogue try to set Charlotte up and Samantha continues to help Smith with his career.
Carrie and the girls are meeting for their usual breakfast when two bombshells are dropped. The good news is that Charlotte and Harry are engaged... but the bad news is that Berger dumped Carrie via a Post-it note earlier that morning. Carrie swears that she will refrain from giving Berger the satisfaction of an angry message, but winds up inadvertantly leaving one after badmouthing him to some of his friends at an exclusive club.
An assignment sends Carrie to explore the newest pastime for singles in New York... swinging through the air on the flying trapeze. Try as she might, Carrie just can't allow herself to let go of the bar and allow her instructor to catch her. While relating this situation to the girls, Harry appears and introduces Carrie to his best man for the upcoming nuptials. After much coaxing, Carrie allows herself a one-nighter with her fellow member of the wedding party, but winds up wildly unsatisfied after he proves to be a less than sensitive lover.
Carrie and Stanford attend a baby shower thrown by their friends Kyra and Chuck. Upon arriving, they discover that Kyra's house rules include the removal of all footwear, regardless if doing so will destroy a carefully crafted outfit. The evening is pleasant enough, but when Carrie plans to leave the party, she discovers that her brand new Manolos have been stolen. Later, Kyra offers to pay for the missing shoes, but balks when she discovers that they cost 5. Carrie winds up leaving the apartment with no compensation, and a sense of shoe-induced shame. She wonders if she has somehow made a mistake by choosing the lifestyle that she did, rather than the more traditional one chosen by Kyra.
Carrie's high school boyfriend, Jeremy, calls Carrie and asks her to go to dinner with him. Carrie is plesantly surprised and begins to reconnect with him until he reveals the real reason that he's in town. Samantha is unable to get into a new SoHo club but soon finds away to get in. Charlotte and Anthony run into Stanford and Marcus, and at lunch, Charlotte reveals something that leads Marcus to break up with Stanford. Meanwhile, Dr. Leeds moves into Miranda's building and the two get closer.
Big returns to New York for a angioplasty and Carrie is upset when she hears the news. However, after the surgery, Carrie does her best to help Big recover. Samantha and Smith's relationship becomes awkward when Smith tries to hold Samantha's hand while they're in public. Meanwhile, Miranda stresses over how to tell Steve about her new relationship, but Steve finds out for himself when he walks in on the two. Charlotte decides to try Eastern medicine to help her problems with getting pregnant.
At an art exhibit, Carrie meets Aleksandr Petrovsky, an artist, who soon asks her out. Charlotte is devastated when she and Harry finally conceive, but she miscarries. Robert tells Miranda that he loves her, through cookies, making Miranda think that she may never be able to express her feelings. However, this proves to be untrue at Brady's first birthday party. Samantha finds gray hair 'down there' and dyes it to cover up the grays, but the dye job goes bad.
After much consideration, Carrie decides that she will begin sleeping with Petrovsky, but rejects Charlotte's suggestion that an actual relationship between the two could develop. The pair spend a wonderful night together, but the next morning, Carrie is shocked to find that Petrovsky's apartment is also a hub for his business, with a living room full of his employees. Petrovsky serves Carrie a wonderful breakfast, but she wonders if she's just the latest in a long line of conquests for the artist.
The relationship between Carrie and Petrovsky continues to develop, but one thing continues to nag at Carrie. Petrovsky is given to grand gestures of affection (including poetry reading and the composition of original love songs), and that's a bit too much for this slightly cynical New York girl. When Petrovsky takes Carrie to a premiere at the Met, she literally swoons. To balance things out, the artist takes her to McDonald's, where the pair become the most elegantly dressed duo in the establishment's history.
Carrie learns that Petrovsky has a 22 year-old daughter and doesn't want any more children, leaving Carrie to wonder if she's willing to give up children for Petrovsky. At her cancer treatments, the male physician offends Samantha, so Samantha sets out to get on a female doctor's schedule. Miranda and Steve leave for their honeymoon, but the location Steve chose drives Miranda crazy. Brady is left in the care of Carrie and Charlotte, and Charlotte stresses out the entire time.
Carrie and Petrovsky have dinner together, but Carrie walks out on him when he talks about a friend he had that died of cancer. Samantha's treatments go well, except for the fact that her hair starts to fall out. Smith helps her feel better when he shave his head, and the two go out together, both bald. Charlotte and Harry continue to have trouble conceiving, and Charlotte ends up adopting a dog. Meanwhile, Steve and Miranda look at houses in Brooklyn after they both feel that the apartment is too cramped.
Carrie and Petrovsky's relationship continues to fall apart. In order to prove that Smith is not gay, Samantha tapes them having sex and "accidentally" leaks it to the press. Meanwhile, Charlotte enters her dog in a dog show and Miranda has a hard time adjusting to her life in Brooklyn.
At a dinner party, Petrovsky breaks the news that Carrie is moving with him to Paris, and Miranda doesn't take the news well. A death at a party causes Carrie to re-examine her life, and the girls' lives, in order to make a decision about Paris.
Before leaving for Paris, Carrie runs into Big and tells him that she wants him out of her life. After one last dinner with the girls, Carrie leaves for Paris. In New York, Samantha speaks at a breast cancer benefit and Charlotte goes to Carrie's in search of an adoption recommendation, but ends up talking to big instead. After talking with Miranda, Samantha and Charlotte, Big decides to go to Paris after Carrie.
Carrie has an awkward meal with Petrovsky's ex-wife and begins to wonder if she can ever live up to his ex. On the streets, Carrie meets some of her fans who want to throw Carrie a party. In New York, Samantha drives Smith away when her sex drive begins to fade, but Smith lets Samantha know that he has strong feelings for her, even when she has no sex drive. Charlotte and Harry finally receive good news about their adoption. Steve and Miranda agree to let his mother live with them after she has a stroke. Back in Paris, Petrovsky ends up slapping Carrie during a fight, and runs into Big, who is there to help her pick up the pieces.