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She immediately rectifies that situation, which ends up backfiring when Sam grows much too attached to Ms. Now: Jacob Pitts played sex-obsessed Cooper Harris in the cult comedy classic Then: Sports doctor Robert Leeds was Miranda's (handsome) neighbor who, after some elevator flirting, became her (handsome) serious BF. Now: Nick Scotti was a popular male model when he met Madonna at a party thrown by photographer Herb Ritts.She took a liking to him and catapulted him to It Boy status; alongside his .He's sensitive (if simple) and dreams of being a small-town sheriff.

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Now: Bradley Cooper has three consecutive Best Actor Oscar nominations under his belt, he dates models, and he's still hot. Then: When Charlotte decides to relive her 20s during a weekend in the Hamptons, Long Island ice tea hangovers are the least of her problems.

Instead, she ends up with a mortifying case of crabs and it's hard to even watch that episode without feeling itchy.

He has continued to work steadily on shows like Then: Remember home phone lines?

After being inundated with messages to RSVP for a party being thrown by another Sam Jones, Samantha tracks down her namesake and discovers that Sam is a hopeless college virgin. Leeds could do no wrong, from his giant "I Love You" cookie declaration to tending to Miranda when she caught chicken pox from Brady. Now: Blair Underwood continues to be a successful actor on stage and screen, including a stint as Stanley in a Broadway production of Then: There's no way to sugarcoat it: This was the package delivery guy Samantha was blowing when Carrie walked in on her, and then they had a big fight over Carrie being judgmental (which she totally was! Samantha chalked up the misadventure to her hurt feelings about Richard, but she may have been onto something — there's nothing worse than that little "missed courier" sticker, right?

They jump into his Porsche for what looks to be a sure thing, until he spots her magazine cover at a newspaper stands and she's confronted with her own insecurities.

Also, he's kind of a jerk and doesn't let her out of the car (luckily it's a convertible).

After a spin-the-bottle smooch with guest star Alanis, Carrie decides that anything-goes sexuality is not in her wheelhouse (but over-the-thigh gold boots definitely were).

Now: Eddie Cahill's guest stint proved to be a jumping off point for steady TV work; he was a regular on Then: Still a little sad from the Post-it note read 'round the world (whatevs, Berger, you're not even on this list!

They look like they are on a one-way street to Makeoutville until Louis expresses his dislike for one of Carrie's greatest loves, New York City. Now: Daniel Sunjata starred as a firefighter on long-running drama Then: On an "off" weekend with Mr.

Big, Carrie bops around town with a very young, very cute, and very pierced dude.

When Samantha stops going down on her sex partner, she has to gently explain to him that it's because his bodily fluid is high on the "retch" meter. Now: Actor Bobby Cannavale is dating one of our favorite actresses, Rose Byrne (they currently star in Then: After giving her hotshot stockbroker neighbor Chip Kil-Kenney a very warm welcome basket (her vagina), Samantha reaps the benefits of his financial expertise with postcoital insider trading tips.