Sex and the City is all about Carrie, Miranda, Charlotte, and Samantha’s differing approaches to relationships. While Carrie might want to talk a lover’s ear off all night, fans know the vivacious Samantha Jones as a girl who’d likely get up to far more adventurous things. But, despite her many flings and experiments across the show’s six seasons, Samantha rarely experiments with romantic relationships.

Everything changes when she falls—and falls hard—for charismatic hotel executive Richard Wright. It’s a romantic about-face for the glamorous PR maven, and, although their relationship isn’t always smooth sailing, it stands out as one of the show’s most significant partnerships. For fans of the pair, certain episodes across the series’s final three seasons perfectly tell the couple’s story.

10 “Just Say Yes” (Season 4, Episode 12)

Samantha and Richard’s working relationship proves to be intense right off the bat, with the PR professional letting her work speak for itself, while Richard remains on high alert for any minor slip-ups. Impressed by her no-nonsense attitude, Richard begins warming up to Samantha and promises of fine dining and travel have Samantha warming up in return. This episode sees the pair’s relationship turn from a cold and grudging business partnership to a promising sexual fling.

9 “All That Glitters” (Season 4, Episode 14)

Samantha finds herself waiting by the phone for Richard and is disturbed by unfamiliar feelings of dependence. Things are made worse when she unwittingly yells a confession of love during sex under the influence, and Richard misunderstands her “I love you” as mere babbling.

A typically-detached Samantha is alarmed by the emotional turmoil that comes with romantic involvement and is ultimately disappointed in the way that her vulnerable admission came across. Fans see Samantha—and she sees herself—in a brand new light in this landmark episode for the character.


8 “Unoriginal Sin” (Season 5, Episode 2)

Richard finally talks his way back into Samantha’s life after a messy breakup, insisting that fear led him to cheat and hoping to make up for his indiscretions with a hefty diamond ring. The relationship appears changed, with Richard focusing exclusively on Samantha and agreeing to standard boyfriend duties such as accompanying her to Miranda’s baptism.

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In this meaningful episode, a light appears at the end of the tunnel as the couple’s relationship appears to be on solid ground for the first time in a long time.

7 “Anchors Away” (Season 5, Episode 1)

In the season five premiere, Richard relentlessly calls Samantha with countless apologies, but the girls encourage Samantha to cut him out of her life. Samantha agrees to meet up and arrives dressed to the nines, only to throw a drink in Richard’s face. Not fulfilled in her quest for revenge, Samantha prints slanderous posters and distributes them in Richard’s neighborhood.

Fans would expect Samantha to move on easily, but, when her friends are paired off on the dance floor and the thrill of payback wears off, Samantha finds herself comforted by Richard’s voicemails.

6 “Ring a Ding Ding” (Season 4, Episode 9)

Samantha is pleased to accept Richard’s luxurious gifts but is disappointed by his impersonal greeting cards. When Samantha unmasks Richard’s personal shopper as the cards’ true author, she secretly convinces him to sign the next one in a more committed tone.

When Samantha’s plan yields a forced confession of love from Richard she responds that she loves her gift, happy at having gained the emotional upper hand. A relationship newbie despite her years of experience, Samantha begins playing games that she

5 “Let There Be Light” (Season 6, Episode 13)

Tired of Smith’s boyish charm, Samantha longs for the strength and security of a mature lover. When he invites her to a party hosted at one of Richard’s hotels, Samantha excitedly accepts. Smith, too meek to even cut in line, is easily overshadowed by Richard, who sweeps his ex Samantha off her feet. While Smith fraternizes with the young crowd, Sam spends the evening in Richard’s company, eventually agreeing to follow him up to bed.

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In the end, Samantha is touched by Smith’s commitment and compassion and realizes that Richard’s callous strength that she craved wasn’t nearly as nice as she’d remembered.

4 “Luck Be An Old Lady” (Season 5, Episode 3)

At Richard’s invitation, the girls take a trip to Atlantic City, one which becomes a hassle for Samantha when she’s faced with all the beautiful women at their hotel.

Anxious once again at the thought of Richard’s infidelity, Samantha does everything she can to catch him in the act. She finally decides to call it quits when she realizes the daily pressures that a relationship with Richard will inflict on her. Samantha finally comes to terms with what must be done, and this time the couple’s breakup is final.

3 Belles of the Balls (Season 4, Episode 10)

Far from a typical meet-cute, the couple’s first encounter reduces Samantha to tears. When her connections land her a meeting with renowned hotel magnate Richard Wright, Samantha is upset at the meeting’s sexist and dismissive tone. Driven to prove herself, Samantha persists until Richard finally validates her claim to the position, but he declares her to be unhireable due to her romantic history with his architect.

Ultimately, Richard is left impressed by her nerve and professional competence, and a testy professional relationship is born.

2 “The Good Fight” (Season 4, Episode 13)

Navigating a fine line between professional employee and casual lover, Samantha is enamored by Richard’s silver tongue and sexual prowess. Unusually for Samantha, she’s so taken that she finds herself engaged in risky sex in her new fling’s open-concept office.

She later abandons the girls to join Richard at his rooftop pool, where the two take a romantic skinny dip in an iconic scene that sees the couple take their purely physical relationship even further. As the pair shares a poolside slow-dance, Samantha lowers her defenses and finally acknowledges her developing feelings for Richard.

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1 “I Heart NY” (Season 4, Episode 18)

Samantha feels neglected due to Richard’s flighty lifestyle and desires a more involved relationship. She lays her cards on the table in the form of a heart-themed triptych but receives a lukewarm reception from Richard. Feeling dejected, Samantha snaps at Richard and accuses him of cheating, which he vehemently denies.

Taking matters into her own hands, Samantha dons a disguise and follows Richard, eventually walking in on him mid-romp. In a fit of rage, Samantha shatters the heart print and declares both their hearts broken. Fittingly for a season finale, this episode finds Samantha facing her first truly devastating breakup of the series.

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