20 best moments from Sex and the City

14 of 21

For Samantha, size really does matter (“Oh Come All Ye Faith”)

Samantha is a connoisseur of all things sex, and she knows a thing or two about the male body (one part in particular). She once dated a man they dubbed Mr. Too Big, who was so well-endowed that even Samantha couldn’t handle it all, and had to end things. But in this case, Samantha was dating someone who was more of a Mr. Too Small.

When Samantha starts dating James, there’s an immediate problem. He’s the opposite of Mr. Too Big. She tries to make it work, because she actually really likes the guy, but she just can’t get past the fact that he can’t satisfy her with that thing. “Who cares? His d*ck is like a Gherkin,” she tearfully tells the girls in the bathroom one night.

Samantha realizes how much size really matters to her, and she’s afraid to talk to James about it. How exactly would you approach that topic without coming off as judgmental or hurting the other person? She even cries while they’re making love, and tries to pass it off as happy tears.

They try to go to couples counseling, but Samantha still doesn’t want to admit what the real problem is. After their session, the idea of Samantha having to meet with this doctor every week was too much, and she blurts out “Your penis is too small.”

She finally mentioned the unmentionable, and James reacted exactly how she expected. He responded “Did you ever stop to think that maybe your vagina is too big?” and then stormed out of the room.

We have to hand it to Samantha. She really tried to make this situation work, but in the end, it was something that she just couldn’t work with. Poor guy, though.