Valley of the Twenty-Something Guys: Jennifer Marie Stranges

Carrie and Mr. Big finally decide to meet - on purpose. They've been bumping into each other all around Manhattan, but when they finally set a "date", Carrie is left to wonder if it really is a "date". Mr. Big's ambiguity drives her crazy the entire episode, leaving her to analyze his tone in voice messages and seek the company of a younger guy named Sam that she meets through her friend Samantha.

Carrie relives her youth while dating Sam, as he's a lot younger. Being with Sam reminds her of how good just kissing can really be. Although her and the other women wonder what the wide variety of twenty-something guys would see in them, they take advantage of the opportunity and date younger man. The men in the episode testify that older women are grateful, give great head, know a lot about wine, remind them of their mothers, and know who they are/what they want. Carrie enjoys dating Sam, as proved when she ditches Miranda and a meeting with her editor to go shopping with him, but realizes she's too old to be dating a younger guy when she wakes up in his "twenty-something apartment": pizza boxes, no toilet paper, and roommates, oh my! Samantha jumps off the bandwagon as well when her twenty-something guy acknowledges the wrinkles in her neck.

Charlotte isn't dating a younger guy in this episode, but she's dating someone who wants to try something new - anal sex. Charlotte seeks the support of all her friends in a cab ride and needs their help to make her decision. Although her new lover has her "big 3"- looks, manners and money - she is uneasy with being the up-the-butt girl, because a wife isn't that kind of girl.

The episode ends with Carrie bumping into Mr. Big again, and him inviting her out on an official date. The episode eventually affirms the belief that we should date someone our own age.