Sex and the City chronicles the life of Carrie Bradshaw (Sarah Jessica Parker), a sex and relationship columnist, along with her close-knit circle of friends as they navigate the complexities of love and friendship amid the vibrant backdrop of 1990s and early 2000s New York City. This iconic series is lauded for its authentic portrayal of female friendships and the subtleties of modern relationships, providing a pioneering female viewpoint that was largely absent in media of its time. Although the bond between Charlotte York (Kristin Davis), Miranda Hobbes (Cynthia Nixon), Samantha Jones (Kim Cattrall), and Carrie forms the crux of the narrative, the debate surrounding the most memorable boyfriends in the series remains a lively subject of discussion.
Throughout its six seasons, the quartet experiences various romantic escapades and relationships. Among the myriad of romantic interests, standout characters include Samantha’s partner who shows unwavering support during her cancer battle, Carrie’s fiancé who undertakes a complete renovation of her apartment, and Charlotte’s second husband who adores her unconditionally. The polarizing stories surrounding Carrie and Mr. Big— a character representing the complexities of commitment—continue to captivate both nostalgic and newer audiences alike. The nuanced representation of relationships is a cornerstone that resonates powerfully with fans even after all these years.
10 Trey MacDougal
Charlotte’s First Husband
Trey MacDougal (Kyle MacLachlan) emerges as Charlotte’s initial husband. After resolving to get engaged within the year, Charlotte meets the affluent doctor Trey in Season 3 of the series. Their whirlwind romance quickly leads to an engagement; however, they opt to defer physical intimacy until their wedding night and delay meeting relatives until after their commitment. This decision ultimately backfires as they find themselves lacking foundational discussions essential for a successful marriage. Trey’s detachment from Charlotte’s emotional needs adds a layer of humor to their rocky relationship.
Although Trey struggles with issues in the bedroom, his most significant flaw lies in his failure to confront his overbearing mother, Bunny (Frances Sternhagen). Bunny’s disdain for Charlotte highlights her ability to infantilize Trey, effectively preventing him from taking on adult responsibilities. Although Trey loves Charlotte, it becomes evident that he needs to address personal issues before entering marriage. This revelation comes to a head when Charlotte discovers him inappropriately reliant on his mother.
Despite parting on somewhat amicable terms, the couple ultimately recognizes their differences and Trey’s lack of social maturity. On the upside, their divorce introduces Charlotte to a divorce lawyer who leads her to discover a true love in the future.
9 Mr. Big
Carrie’s On-And-Off Lover And Endgame
Mr. Big, or John James Preston (Chris Noth), stands as one of the most controversial figures in the series. His tall, dark, and enigmatic persona captures Carrie’s attention from the outset when he initially dismisses Samantha to pursue a conversation with her. Their first car ride is iconic, with Carrie seeking insight into Big’s views on love, to which he responds with his unforgettable “abso-f*ckin-lutely.”As their relationship develops, it quickly becomes apparent that Big intentionally keeps Carrie at a distance, creating emotional barriers.
His reluctance to integrate her into his life becomes evident when he opts for secluded dinners and introduces Carrie merely as “a friend”to his mother during an unexpected encounter. Compounding the toxicity of their relationship is Carrie’s discovery of Big’s infidelity with his first wife. His commitment fears intertwine with his inability to appreciate Carrie’s freedoms as a writer, leading to an emotionally taxing dynamic. Their interactions reveal their penchant for toxicity, magnified by a secretive affair during Big’s second marriage.
This tumultuous pattern proves distressing for Carrie while Big frequently moves on to other relationships without consequence, culminating in their reconnection in the Paris finale. This reunion, although celebrated, prompts debate over Big’s character growth—or lack thereof—throughout the entire series.
8 Aleksandr Petrovsky
Carrie’s Last Boyfriend Before Her Final Reunion With Big
Aleksandr Petrovsky, portrayed as an older Russian artist, enters Carrie’s life through Charlotte, who works as an art dealer. Carrie’s attraction to his romanticism and sophistication marks a turning point, contrasting sharply with her experiences with Big. However, as their relationship unfolds, distinct differences emerge.
Their romance culminates in an extended stay in Paris, where Petrovsky’s desire to relocate for work and to be closer to his daughter from his previous marriage complicates matters for Carrie. While Carrie initially enjoys the experience, the interplay of Petrovsky’s work hours and her absence of employment leads to a sense of isolation in a foreign city.
This tension escalates, climaxing in an argument that culminates in violence—Petrovsky slapping Carrie—signaling the end of their relationship. As she grapples with loneliness, an unexpected voicemail from Big to Charlotte nudges him to reconnect with Carrie, setting the stage for a potential reunion.
7 Maria Diega Reyes
Samantha’s First And Only Girlfriend
Maria Diega Reyes (Sônia Braga) emerges as Samantha’s only female love interest, introduced through Charlotte. Their relationship highlights Samantha’s evolving sexuality throughout the series. Although it is passionate, it becomes apparent that Maria views relationships with more seriousness than Samantha, creating a natural tension.
In a modern context, this storyline would be approached with greater sensitivity and depth. Samantha ultimately ends the relationship, recognizing her inclination towards men, which leaves it feeling somewhat experimental. Today’s narratives for LGBTQ+ characters typically embrace richer portrayals, as evidenced by Miranda’s journey in the sequel series, And Just Like That.
Maria’s influence on Samantha is profound, allowing her to explore her identity, yet they unravel due to their incompatibility. While Samantha grows through the experience, Maria deserves a partner willing to fully immerse themselves emotionally.
6 Steve Brady
Miranda’s Husband
Steve Brady (David Eigenberg) is introduced as a ruggedly charming bartender from Queens, whom Miranda meets after a frustrating experience with Carrie. The two engage in witty exchanges, eventually leading to a relationship filled with ups and downs, starkly different from Carrie and Big’s dynamic. Steve, despite his down-to-earth nature, exhibits bouts of toxicity stemming from his insecurities regarding Miranda’s accomplishments.
Miranda, a successful Harvard-educated lawyer, faces challenges related to her own trust issues. Steve’s personal deficiencies present continual obstacles in their relationship, including his immaturity as he neglects household responsibilities and fails to prioritize Miranda during her pregnancy. Although he ultimately matures and offers his support, the sacrifices Miranda makes for their relationship highlight underlying inequalities.
5 Dr. Robert Leeds
Miranda’s Last Boyfriend Before She Marries Steve
Dr. Robert Leeds (Blair Underwood), a physician associated with the New York Knicks, becomes Miranda’s first legitimate match. As intelligent and supportive, he encourages Miranda to embrace life beyond her career. Despite his genuine affection for her and willingness to be involved with her son, Miranda ultimately realizes she is still emotionally tethered to Steve.
This realization leads to Miranda leaving Robert to reconcile with Steve, sparking a wave of tension with Robert that underscores their emotional depth. Had Robert been around longer, it seems he could have become one of the series’ most beloved characters.
4 Stephan
Charlotte’s Pastry Chef Boyfriend
Stephan (Dan Futterman) represents the modern sensitive man in Sex and the City, initially appearing as Charlotte’s friend. Mistaken for gay due to his appearance and profession, he later reveals his interest in Charlotte, leading to a unique romantic entanglement. Their relationship hits a roadblock when Stephan confronts a mouse in his apartment, showcasing his extreme reactions.
In today’s context, his character could resonate with a broader audience as straight men in creative fields have become far more usual. His emotional availability and respect for Charlotte’s career could have made for a fitting partnership, ultimately limited by how the show perceived masculinity in the late 90s and early 2000s.
3 Aidan Shaw
Carrie’s Fiancé In Between Flings With Big
Aidan Shaw, a furniture designer, captivates Carrie when she visits his showroom courtesy of Stanford (Willie Garson). Easily charmed by his wholesome personality, Carrie even gives up her smoking habit in an effort to build a meaningful relationship. This progression tends to propel Carrie toward maturity, yet she struggles to fully embrace Aidan’s stability.
Although Aidan yearns for commitment, Carrie finds herself torn between his grounded nature and Mr. Big’s exciting unpredictability. This conflict results in Carrie cheating on Aidan and later reconciling, getting engaged with his help on her apartment renovations. Yet, despite Aidan’s commendable attributes, the relationship ultimately reveals an inherent disconnect.
After the loss of Big in the follow-up series, And Just Like That, Carrie reconnects with Aidan, who has experienced significant life changes. Their rekindled romance injects uncertainty regarding their potential to bridge past divides, revealing how personal growth shapes their interactions.
2 Harry Goldenblatt
Charlotte’s Second Husband
Harry Goldenblatt (Evan Handler) steps onto the scene as Charlotte’s divorce lawyer, transforming into her second husband. Their unexpected romance unfolds after Harry openly expresses his feelings for Charlotte following her divorce. Initially establishing a friendship during the legal proceedings, their relationship blossoms into something deeper, but cultural differences arise as Harry seeks a Jewish partner.
Charlotte’s decision to convert to Judaism signifies her growth, reflecting her emotional evolution as well. The couple emerges as the most balanced partnership on the show, characterized by mutual respect and understanding. Their willingness to compromise redefines their bond in a way that starkly contrasts with the tumultuous relationships of their friends.
1 Smith Jerrod
Samantha’s Last Boyfriend
Smith Jerrod stands out as Samantha’s most noteworthy romantic interest. He is introduced as an aspiring actor working in a prestigious restaurant. At the restaurant opening, the charming Smith captures Samantha’s attention, igniting a relationship that evolves into emotional depth.
Samantha, known for her casual affairs, finds a unique connection with Smith, who balances ambition with sincerity. As their relationship grows, he prospers in theatre while maintaining his commitment to sobriety—qualities that make him an exceptional partner for Samantha. During her battle with breast cancer, Smith makes the ultimate gesture of love by shaving his head in solidarity with her, showcasing his emotional investment.
This bond allows Samantha to open up emotionally, creating a rare space for vulnerability in her life. Despite their ups and downs, Smith reflects everything a partner should be—offering security, affection, and unwavering support, making him a benchmark for the other male characters in the series to strive toward.
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