Season 1, Episode 4: Valley of the Twenty-Something Guys
"Shouldn't we be dating men our own age?"
After Carrie and Big keep bumping into each other at social events, they finally make plans to see each other. Is it a date? Is it a thing? Who knows, because he's always bailing early or bringing along a friend. While Carrie waits for Big to decide what they're doing, she starts hanging out with twenty-something Sam. Miranda and Samantha are also dating/sleeping with twenty-something guys. Carrie gets a rush from making out with her younger man all over the place, but eventually sees his twenty-something lifestyle for what it is. (Hint: Using toilet paper as a coffee filter.) Charlotte has a dilemma when her latest picture-perfect man asks her to have anal sex. (Spoiler Alert: She declines.)