As Fleet Week kicks off in New York City, Carrie, Samantha and Charlotte begin to adjust to Miranda's new life with baby Brady. Samantha is finding it hard to adjust to "cleaning up her act" in front of Brady, especially since she's still seething over Richard's infidelity. Newly single Charlotte is ready to find her next great love, whereas Carrie wonders if after Big and Aidan, she's all out of great loves. She asks: When it comes to being carefree single girls, have we missed the boat?
Carrie turns to Manhattan for romance, at first reveling in her amorous relationship with the city but then feeling the lonely side of dating NYC. The only company that she can find is a fellow single woman, albeit a much older one who likes to mix her prescription drugs in with her ice cream. When a chance encounter with a sailor yields an invite to the Fleet Week party, Carrie jumps at the opportunity.
Meanwhile, Samantha is on a mission to get back at Richard. First she throws a martini in his face and then plasters his neighborhood with posters calling him a cheater and liar. Richard isn't fazed and persists in apologizing to Sam and professing his love for her.
While Miranda works on the art of breastfeeding, Carrie, Samantha and Charlotte go party with some studly sailors. Charlotte flirts with an officer who isn't quite a gentleman. And despite a Southern sailor's best efforts, Carrie goes home alone, realizing that until she lets go of the past and finds her true love, dating New York will be just fine for now.