5 Timeless Sex and the City Episodes & 5 We Want to Forget

5 Timeless Sex and the City Episodes and 5 We Want to Forget

Welcome to MsMojo, and today we couldn’t help but wonder: Which episodes of this iconic HBO series can we easily watch again and again, and which would we rather pretend didn’t exist?

#5: Timeless: “A Woman’s Right to Shoes”

Time and time again, Carrie, Miranda, Charlotte, and Samantha deal with being scrutinized for their singleness. Baby showers, weddings, engagement parties, and even apartment signings have been moments where their accomplishments don’t seem to matter because they don’t have a husband or children. When Carrie’s Manolos are stolen at her friend’s party, the host offers to pay her back for the shoes until she hears the price tag. Hearing her judge Carrie for spending that much money on her husband-less, baby-less self still strikes a nerve. However, Carrie finds the perfect way to get her shoes back and make a point for single women everywhere.

#5: Forget: “Models and Mortals”

In this early episode, we’re still in the days of Carrie breaking the fourth wall. Unfortunately, she does so to rally off some stereotypical depictions of women who work as models. The episode can’t seem to resist depicting models as materialistic and unintelligent sex objects who make “normal” people feel bad about themselves. It gets worse. Carrie pays a visit to an artist friend whose masterpiece is a video collection of models being intimate with him, recorded without their consent. Every show needs time to find its footing, but the very second episode of “Sex and the City” could have used a few more rounds of editing.

#4: Timeless: “Secret Sex”

This episode is a perfectly nostalgic snapshot of single life before things get too serious. Carrie’s romance with Big is just getting started, and her photo shoot for her column’s bus ad comes with an amazing perk — she gets to keep the dress. As we’re still getting to know the women, this early episode offers a look into their unique perspectives and personalities. Charlotte’s surprising fling and Miranda’s boldness with a date are standout moments. But the classic sequence is the hangout at Carrie’s apartment where everyone shares their two cents on having sex on the first date.

#4: Forget: “What’s Sex Got to Do with It?”

The central message of this episode is a bit of a mixed bag as everyone tries to get a handle on the importance of sex. There’s a spontaneous fling between Carrie and Ray the jazzman, a sort-of-married fling between Charlotte and Trey, and an all-consuming fling between Miranda and… chocolate. Samantha’s new relationship with Maria is the storyline with potential in this episode, but it takes a disappointing turn. While the girls are rightfully confused to see Samantha committed to someone, their dismissal of her interest in women comes off as unsympathetic and narrow-minded. If anything, Samantha is so open about her sexuality that it shouldn’t have been a surprise to anyone!

#3: Timeless: “Coulda, Woulda, Shoulda”

Samantha’s Birkin curse and Lucy Liu’s guest appearance are enough to make this episode a classic. However, its discussion of abortion is sensitive and complex. In this episode, Charlotte’s discovery that her odds of conceiving naturally are low comes at the same time as Miranda’s surprising pregnancy. When Miranda discusses abortion as an option, Charlotte is furious and Carrie reflects on her own experiences. For Carrie, this comes as an opportunity to deepen her connection with Aidan, and Charlotte and Miranda grow to understand each other a little better. Although their reactions and reasoning may be at odds, this episode highlights the unwavering support and love that friends can offer.

#3: Forget: “Cock a Doodle Do!”

In the third season, the girls go through some painful romantic arcs they’d probably like to forget. Charlotte’s marriage to Trey is deeply strained, Carrie is trapped in a love triangle with Aidan and Big, and Miranda moves in and breaks up with Steve in a matter of weeks. While this episode does include an iconic Carrie and Big moment when they fall into a duck pond, Samantha’s plot line involving the transgender sex workers outside her apartment makes the whole episode difficult to revisit. The jabs at these characters are uncomfortable and unnecessary, and their depiction is an unfortunate punchline that doesn’t help to end this chaotic season on a good note.

#2: Timeless: “My Motherboard, My Self”

When we lose someone or something important, it forces us to reckon with our vulnerabilities. When Miranda’s mother suddenly passes away, the four women show how they cope with grief. Miranda tries to maintain her tough exterior, Charlotte swoops in as an organizer, and Samantha is uncomfortably avoidant. Carrie also faces some harsh truths about her relationship with Aidan. Despite these struggles, the immediate support the women offer Miranda is a testament to their bond. They may be independent women, but that fact doesn’t deny the importance of love and friendship.

#2: Forget: “Boy, Girl, Boy, Girl...”

“Sex and the City” regularly attempted to address modern issues in innovative ways. But that doesn’t mean that every take aged well or was discussed productively. When Carrie starts dating Sean, a younger man who mentions that he’s bisexual, her reaction is less than accepting and more than awkward. Everyone is weirded out by Sean’s openness — well, except Samantha, always a reliable voice for exploration when it comes to sex. This episode could have been the perfect opportunity to examine what made the girls feel skeptical about having a partner who goes both ways, but it leaves a lot to be desired. At least Charlotte’s moment in drag is a silver lining.

Before we unveil our top picks, here are a few honorable mentions.

Forget: “The Big Journey”
Carrie & Samantha on a Cross-Country Train Ride? They Should’ve Stayed in Manhattan

Timeless: “The Agony and the 'Ex'-tacy”
Who Needs Men? Friends Make the Best Soulmates

Forget: “The F**k Buddy”
Carrie Tries to Transform a Friend with Benefits Into a Boyfriend
Forget: “Games People Play”
Proving Your Therapist Right Is Not a Great Look

Timeless: “Running with Scissors”
Carrie & Big’s Affair Hits Its Breaking Point

#1: Timeless: “I Heart NY”

In the months following September 11, 2001, many television shows were faced with the challenge of depicting Manhattan in the aftermath of the tragedy. Although the finale of season four was written before the attacks, it wound up serving as a heartfelt and hopeful tribute to New York City. When Big suddenly announces that he’s moving to Napa, Carrie plans one final perfect New York night with him. Then, in the middle of a carriage ride through Central Park, she leaves him to be with Miranda when she goes into labor. It’s Carrie at her best: romantic, mature, and dedicated to her best friend in her time of need. In her column, Carrie’s message about change and love is enduring.

#1: Forget: “No Ifs, Ands, or Butts”

As one of the first of few nonwhite love interests on the show, Chivon’s introduction gave us some hope that this episode might aim to navigate interracial relationships. Unfortunately, the writing of this episode really misses the mark. The chit-chat the girls have about political correctness and race is uncomfortable, but the racial stereotypes make this episode an easy skip. To really drive this lack of awareness home, in her column, Carrie tries to bring race, smoking, and bad kissing onto the same playing field of relationship dealbreakers. Unfortunately, the fact that this is Aidan’s first appearance doesn’t do much to save this episode.

What “Sex and the City” episodes are your forever favorites, and which ones would you be happy to wipe from memory? Tell us in the comments.