Sex and the City tells the story of sex and relationship columnist Carrie Bradshaw (Sarah Jessica Parker) and her close circle of friends navigating life and love against the backdrop of 1990s and early aughts New York City. The show offered a poignant look at the importance of female friendship and the nuances of modern relationships, offering a groundbreaking female perspective for its time. While the friendship between Charlotte York (Kristin Davis), Miranda Hobbes (Cynthia Nixon), Samantha Jones (Kim Cattrall) and Carie remains its focus, the contenders for the best boyfriend from Sex and the City remains a topic of conversation.
The group of women date and marry numerous men throughout Sex and the City‘s six seasons. However, there are several standouts, including Samantha’s boyfriend, who shaves his head in solidarity when she battles cancer, Carrie’s fiancé, who renovates her entire apartment, and Charlotte’s second husband, who worships the ground she walks on. Most importantly, there are Carrie and Mr. Big, a man emblematic of his era and highly controversial due to his fear of commitment. Needless to say, the show’s varied depiction of relationships is what continues to resonate with new and old viewers today.
10
Trey MacDougal
Charlotte’s First Husband
Trey MacDougal (Kyle MacLachlan) is Charlotte’s first husband. After she sets a goal for herself to be engaged within a year, she meets wealthy doctor Trey in season 3 of Sex and the City. The pair are engaged after dating for a brief period of time, during which they decide to save intimacy for their wedding night and do not meet each other’s families until post-engagement. Of course, this backfires, as they lacked important discussions prior to making such a commitment. Trey is almost humorously out-of-touch with Charlotte’s needs.
He struggles to perform in the bedroom, but the biggest issue is his inability to stand up to his domineering mother, Bunny (Frances Sternhagen). Bunny clearly disapproves of Charlotte, despite Charlotte’s own privileged upbringing, college education, and illustrious career as an art dealer. Bunny infantilizes Trey and allows him to skirt the important responsibilities of adulthood. While Trey loves Charlotte and is eager to commit, it becomes clear he should have worked his own issues out first. Charlotte recognizes this when she walks in on his mother bathing him.
Sex And The City: Carrie & Mr. Big’s Relationship Timeline
Between the original HBO series, the movies, and the revival, Sex and the City’s Carrie and Big had a long, turbulent romantic relationship timeline.
The pair part ways on mostly amicable terms after making their marriage work for a brief period. At the end of the day, they are simply too different, and Trey lacks social skills. On the bright side, their divorce leads Charlotte to hiring a certain divorce lawyer to help her navigate their prenuptial agreement, and meet her true love.
9
Mr. Big
Carrie’s On-And-Off Lover And Endgame
Mr. Big, a nickname for John James Preston (Chris Noth), is one of the most divisive love interests in Sex and the City. Big is on the scene at the very start of the show, as a tall, dark, handsome, elusive, sharp-dressed businessman who first catches Samantha’s eye, but rejects her in a bar in favor of talking to Carrie. The pair share a car ride back to her apartment, where she asks him if he’s ever been in love, and he replies with his iconic “abso-f*ckinlutley.” The pair begin dating, but Carrie quickly realizes that Big is purposely keeping her at arms length and separate from his inner circle.
He takes her out to dinner at restaurants where they won’t be seen. Big tells his mother that Carrie is his friend after they bump into her at church. To make matters worse, Carrie does her own snooping and discovers that he cheated on his first wife. His fear of commitment, combined with his lack of understanding of Carrie’s free-spirited lifestyle as a writer, is often a cocktail for disaster. The couple are often incredibly toxic towards one another, and have an affair during Big’s second marriage to Natasha (Bridget Moynahan).
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They tend to bring out the worst in each other, from insecurities to smoking addictions. Their on-and-off dynamic causes Carrie a lot of emotional distress, while Big is able to seamlessly move on to other women every time until the show’s very end. The Sex and the City finale sees the pair romantically reunite in Paris after Carrie herself sabotages a string of relationships, making the tumultuous couple strangely the perfect match. This still doesn’t make Big a good love interest or character in general, as he sees little growth throughout the show.
8
Aleksandr Petrovsky
Carrie’s Last Boyfriend Before Her Final Reunion With Big
Aleksandr Petrovsky is an older Russian artist who Carrie meets through Charlotte, who is an active art dealer. Carrie admires his romanticism and elegance, as he often treats her to extravagant dates and invites her into his home. Petrovsky feels refreshing to viewers for his honesty with Carrie and his willingness to open his life to her, the opposite of Big. However, as their relationship progresses, their differences begin to show.
Their relationship culminates in an extended stay in Paris for an exhibition, where Petrovsky wants to move for his work and to be closer in proximity to his young adult daughter, Chloé (Cécile Cassel) from his previous marriage to Juliet (Carol Bouquet). This is only the beginning of many surprises for Carrie during her time in the city.
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Sex and the City: All 4 Of Carrie’s Boyfriends, Explained
Carrie Bradshaw had four real relationships during Sex and the City. Here’s a breakdown of her boyfriends and how their relationships went.
While Carrie gets along with Juliet, Chloé’s snobby attitude towards her makes her feel all the more lonely about living in Paris. As Petrovsky works long hours at the gallery and Carrie has given up her column to move to Paris with him, she is left without a job and friends in a foreign country. Petrovsky is an interesting character, but another Sex and the City man with little character growth. He does not have much of a personality outside his art, and his incompatibility with Carrie and general snobbery place him lower on the list of the show’s love interests.
The pair have a heated argument about this that leads Petrovsky to slap Carrie, effectively marking the end of their relationship. As Carrie struggles to cope with everything alone, Charlotte catches Big leaving a voicemail on Carrie’s answering machine when she goes to check on her vacant apartment. This prompts Big to meet with her friends back in New York City, telling them “you three know her better than anyone. You’re the loves of her life.” Finally, having earned their respect, Miranda tells him to “go get our girl.”
7
Maria Diega Reyes
Samantha’s First And Only Girlfriend
Maria Diega Reyes (Sônia Braga) is a lesbian artist who Samantha meets through Charlotte. Samantha is the one character from Sex and the City’s original run whose sexuality is ever-evolving. She begins an eye-opening relationship with Maria, and is as passionate as it is fleeting. It becomes clear that Maria takes her relationships far more seriously than Samantha does.
In today’s world, this arc would have been handled with far more care. Samantha breaks up with Maria after realizing that she does prefer men romantically, leaving the relationship feeling like an experiment. Now, LGBTQ+ characters tend to be written with far more complexity and understanding of the community, as can be seen with Miranda’s journey in the Sex and the City sequel And Just Like That.
Now, LGBTQ+ characters tend to be written with far more complexity and understanding of the community.
While Maria does push Samantha out of her comfort zone by way of allowing her to feel more in tune with herself, they are ultimately incompatible, and Maria deserves someone ready to jump in with her headfirst. Her story line could have been more fleshed out into an interesting character arc, but television did not have as much understanding of navigating LGBTQ+ storytelling at the time.
6
Steve Brady
Miranda’s Husband
Steve Brady (David Eigenberg) is a charming bartender from Queens who meets Miranda at his bar when she drops in for a glass of wine after Carrie ditches her for Big. The pair exhange witty banter and eventually strike up a relationship. However, their relationship quickly becomes and on-again-off-again dynamic in a very different way than Carrie and Big’s. While Steve begins as a lovable, ruggedly handsome, down-to-earth character, he also has plenty of his own toxic moments.
Throughout Sex and the City, Steve feels threatened by Miranda’s success. Miranda is a Harvard-educated lawyer who owns her own apartment in Manhattan, and has a thriving social circle. When they meet, Steve is a working-class bartender with no further ambitions. While he eventually opens his own bar with Aidan Shaw (John Corbett), his own inadequacies come in the way of his relationship with Miranda. On the other hand, Miranda grapples with her own trust issues and rigid ways.
Steve has his moments of major immaturity for a man in his 30s. He leaves dirty underwear and dishes lying about, watches cartoons all day, and initially lacks concern for Miranda’s worries about making partner in her firm amid her pregnancy with their son. Steve additionally cheats on Miranda in the 2008 film Sex and the City, which he admits to as the couple embark on therapy together. While Steve eventually changes his ways and becomes a great father to Brady and understanding partner to Miranda, it is always at the cost that she compromises more for him (including moving to Brooklyn).
5
Dr. Robert Leeds
Miranda’s Last Boyfriend Before She Marries Steve
Dr. Robert Leeds (Blair Underwood) moves into Miranda’s apartment building, and the pair strike up a friendship that evolves into a relationship. Robert is a doctor who works for the New York Knicks, and is Miranda’s first and only love interest to truly be up to par with her. He is intelligent, educated, and encourages Miranda to take time to breathe and enjoy the life she has worked so hard for. He is also more than willing to step in with Brady.
Ultimately, Miranda realizes she is not over Steve, and leaves Robert for him. Steve moves back into the building briefly before they buy and renovate a house in Brooklyn. This causes plenty of tension between the couple and Robert, and it seems like his childish reaction felt intentional in inspiring viewers to side with Steve. Had Robert had more time on Sex and the City, he could definitely have evolved into one of the show’s best characters.
4
Stephan
Charlotte’s Pastry Chef Boyfriend
Stephan (Dan Futterman) would have been a Gen Z favorite Sex and the City boyfriend. He begins as Charlotte’s friend, who she assumes is gay due to his personal style and job as a pastry chef. He then reveals that he is straight and romantically interested in her. Confused, Charlotte is open to pursuing a relationship with him, but remains befuddled by his version of masculinity. His relationship with Charlotte comes to a screeching halt when he hilariously screams in fear over a mouse in his apartment.
In today’s world, straight men in creative fields have become far more common, and this plot line would not have gone the same way. Stephan clearly values Charlotte as a person and understands her career as an art dealer, making them very compatible. The only reason the character did not last is that he did not match the stereotypes of masculinity present in the popular media of the 1990s and 2000s. Given his stable lifestyle and emotional availability, Stephan could have been a great partner to Charlotte if the character had more time on the show.
3
Aidan Shaw
Carrie’s Fiancé In Between Flings With Big
Aidan Shaw, a furniture designer, meets Carrie when her friend Stanford Blatch (Willie Garson) invites her to his furniture showroom. Carrie falls for his all-American charm, and even gives up her iconic cigarette smoking habit for him. It becomes clear that Aidan will push Carrie out of her comfort zone and towards maturity and healthy habits, but Carrie is often unable to meet Aidan where he is.
Aidan is mature and ready for a committed relationship and marriage, while Carrie is as well, only not with him. Carrie is often torn between Aidan’s stability and Big’s unpredictability, and ultimately cheats on Aidan with Big. The pair later reconcile and become engaged, with Aidan helping her renovate her apartment. Carrie is constantly put off by his home body ways and even his choice of an engagement ring at first, and it becomes clear that, despite Aidan’s great intentions and strength of character, they are just not a match.
After Big’s shocking death in And Just Like That, Carrie finds her way back to Aidan, now a divorced father of three. It is unclear how their relationship will play out in the new series, as both have grown and matured, but Carrie does not have the experience of raising a family that he does. While they share history, they continue to have very different perspectives.
2
Harry Goldenblatt
Charlotte’s Second Husband
Harry Goldenblatt (Evan Handler) is Charlotte’s second husband, who she first meets when he acts as her divorce lawyer managing her separation from Trey. Their unlikely union comes after Harry declares his love for Charlotte once the divorce is finalized. The pair strike up a friendship throughout the legal process, and Charlotte, feeling appreciative of his affections after her debacle with Trey, initially starts a casual relationship with him. The pair quickly develop romantic feelings for one another, but with one obstacle – Harry is Jewish, and wants to marry a Jewish woman.
This selfless act, coupled with Charlotte’s newfound self-awareness, moves the couple forward.
Charlotte decides to convert to Judaism, in part for Harry and for her own personal journey, while the couple are briefly apart. This selfless act, coupled with Charlotte’s newfound self-awareness, moves the couple forward. In marriage, the couple are arguably the healthiest pairing in Sex and the City. Despite their differences, they love and understand one another for who they are. Unlike many other couples on the show, the pair’s compromises feel far more equal.
1
Smith Jerrod
Samantha’s Last Boyfriend
Smith takes the cake for the best love interest in Sex and the City. He is introduced as a rising actor working at an upscale restaurant to make ends meet. When Carrie is invited to the restaurant’s opening, she brings her girls, and Samantha is immediately attracted to the gorgeous Smith Jerrod. Samantha, who works in public relations and has the most casual relationships out of all the women on the show, finally meets her match in Smith.
The couple’s relationship begins as casual, while Samantha also helps Smith book modeling and acting opportunities. He is kind and hardworking, and works his way up in the local theater scene while maintaining his sobriety from alcohol. He is one of the most stable and self-sufficient men in Sex and the City, despite being younger than most of the other love interests. While Samantha attempts to push him away, he is the only man to truly crack her hard exterior.
She feels comfortable being emotionally vulnerable with him for the first time in the show, and he offers her unconditional support, even when she briefly rekindles with her manipulative ex-boyfriend, Richard Wright (James Remar). This all culminates when Samantha battles breast cancer, and begins losing her hair during chemotherapy. Known in the entertainment world for his long blond locks, Smith voluntarily shaves off his hair in solidarity with Samantha. It is clear that Samantha feels safe in a relationship for the first time, and the other men of Sex and the City certainly could have taken notes.
Sex and the City (2008) is a romantic comedy film that continues the story of Carrie Bradshaw and her friends from the popular television series. Directed by Michael Patrick King, the movie reunites Sarah Jessica Parker, Kim Cattrall, Kristin Davis, and Cynthia Nixon as they navigate love, friendship, and career challenges in New York City. The film explores themes of relationships and personal growth while maintaining the show’s signature style and wit.
- Director
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Michael Patrick King
- Release Date
-
May 12, 2008
- Studio(s)
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New Line Cinema
, HBO - Distributor(s)
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Warner Bros. Pictures
- Writers
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Michael Patrick King
, Candace Bushnell
, Darren Star - Cast
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Sarah Jessica Parker
, Kim Cattrall
, Kristin Davis
, Cynthia Nixon
, Chris Noth
, Candice Bergen - Runtime
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145 minutes
