Three weeks into her relationship with Aidan, Carrie begins to freak because everything seems so perfect. When Aidan asks Carrie to meet his parents, she can't deal and finds herself saying no. Meanwhile, Charlotte presses on in her mission to be married by year's end. Her latest tactic involves forcing her married friends to hook her up with single men they know. Charlotte's first date using the new strategy ends up being a married friend who professes his love for her. But after storming out of that date, Charlotte falls down on the street and meets Trey - the chemistry is instantaneous. Miranda continues to settle into her secure life with Steve, pretty much without incident (except for the "skid marks" in his underwear). Samantha sleeps with a doctor named Mark, who doesn't "need" Viagra, but takes it to spice things up in bed. Intoxicated by the idea of an even more thrilling sexual experience, Samantha pops a pill or two. After a few trysts, Mark suggests they try it without the aid of medical enhancers, but Samantha refuses. Nervous she may get cut off, Samantha asks Mark to write her a prescription for her own supply. While at the opera with Charlotte, Carrie spots Big and Natasha in the balcony and leaves. Big sees her and tries to catch her, but Carrie's long gone. Carrie realizes that in her relationship with Aidan, she's been behaving like Big, and he's been acting like the sensitive and available guy she always wanted Big to be. In a rush to try and undue any damage done, Carrie shows up at breakfast with Aidan and the family.

While he continues to try and find an apartment in New York City's overpriced real estate market, Steve has taken up residency on Miranda's couch. Despite his lack of an apartment, Steve finds a new romantic interest, which saddens Miranda and makes her wonder what she's doing wrong. Charlotte is mixed with bittersweet feelings herself: she's now engaged to Trey, but it didn't happen the way she envisioned. Charlotte ended up proposing to Trey, whose response was "alrighty!" Charlotte is rather devastated, until a few days later when Trey spontaneously suggests they go to Tiffany's to buy the most beautiful engagement ring they can find. Samantha's latest sexy professional, Adam, is great except for the "funky tasting spunk." When she refuses to go down there on a future date, Adam gets annoyed, and Samantha is forced to spell it out for him. Adam thinks she's just making excuses, so Samantha challenges him to taste it for himself. Meanwhile, Carrie bumps into a drunk Big at a furniture show. He blurts out that he and Natasha are not working out. If that wasn't enough, he calls Carrie several times, and learns from Aidan she's working on a deadline at a hotel next door. Big shows up at the hotel, and drops the bomb: he says he's made a mistake, and he really loves Carrie. Carrie runs for the elevators, but Big pushes his way in, which leads to the bedroom, which ends with sharing a cigarette in bed.