Carrie Bradshaw may be a successful sex columnist on Sex and the City, but she’s highly unsuccessful in the love department, with every romance ending for various reasons. For six seasons, Carrie has loved, lost, and had random hookups in the beloved HBO series. Now that And Just Like That will be returning for a second season, there’s the potential for revisiting some of Carrie’s former flames.
And Just Like That cuts Carrie’s voiceovers that so famously chronicle her romantic relationships in Sex and the City. Carrie’s misadventures in love bring a questionable cast of characters. Some men are more forgettable than others, but every romance plays a role in Carrie’s romantic ending with her true love.
21 Sean The Marrying Guy
Sex and the City has fabulous weddings, but Carrie dodges a marriage bullet with her short-lived romance with Sean the Marrying Guy. In season 1 episode “Bay of Married Pigs,” Carrie is introduced to Sean through mutual friends, and they decide to see each other again. However, Sean invites Carrie to a housewarming party where he shows Carrie and Charlotte his den that he plans to turn into a kids’ room and a crib mobile he bought for his future child. Their week-long romance ends over a romantic dinner with Carrie explaining she isn’t on the same page with wanting to settle down quickly.
20 Sam The Twenty-Something
Carrie tries her hand at dating a guy in his twenties. Timothy Olyphant is known for Justified, but he makes a cameo as Carrie’s hookup, Sam, in Sex and the City season 1 episode “Valley of the Twenty-Something Guys.” After hooking up, Carrie is put off from dating men in their 20s. Sam’s apartment is messy, and he is pretty much not an adult yet, not even having toilet paper available for Carrie in the restroom.
19 Gilles
Carrie’s romance with Gilles lasts all of one night. After being introduced to the French architect in Sex and the City season 1 episode “The Power of Female Sex,” Carrie and Gilles find themselves hooking up in her apartment. However, to Carrie’s horror, he leaves $1,000 on her nightstand before leaving. Carrie isn’t a paid escort and, rightfully, never sees Gilles again.
18 Joe Starr
After meeting at a ballgame in the Sex and the City season 2 premier, Carrie goes on a date with NY Yankees player Joe Starr. Unfortunately, Joe is just a blip in Carrie’s complete timeline. Despite hitting it off instantly, Carrie breaks it off with him because she’s just not over Big. Joe is simply Carrie’s rebound to get back into dating.
17 Ben
Ben is the political magazine editor that Carries dates in Sex and the City season 2 episode “The Freak Show.” Considering Carrie’s penchant for writing, Ben and Carrie could have made a good couple. However, he’s normal compared to the string of men Carrie has dated in the past. Carrie isn’t the one to break things off, but Ben breaks up with her after she destroys his apartment in an attempt to find what makes him weird.
16 John McFadden
Carrie has four major boyfriends in Sex and the City, but John McFadden wasn’t one of them. In “The F*ck Buddy,” Carrie tries to make a real relationship out of the purely physical relationship she has with John. The sex is great, but Carrie tries to make a relationship out of nothing. She and John have little in common, and he’s not a great conversationalist.
15 Seth
Played by Jon Bon Jovi, Carrie meets Seth in the waiting room of her therapist’s office in “Games People Play.” The two briefly date and sleep together. Unfortunately, the diagnoses from their therapist get in the way. Carrie dates the wrong men. Seth loses interest in a woman after hooking up. Carrie and Seth are completely wrong for each other and probably should have discussed their diagnosis before sleeping together.
14 Vaughn Wysel
Vaughn is perfect on paper for Carrie. He writes short-stories and has an amazing mother whom Carrie grows close to. Unfortunately, Vaughn has problems performing sexually, and it causes issues in their relationship. Carrie also realizes she enjoys the company of his mother more than his company and feels terrible about their breakup because she doesn’t want to break up with his family.
13 Aidan Shaw
Before Aidan returns in And Just Like That season 2, he was making Carrie swoon in Sex and the City season 3. Carrie’s relationship with the furniture designer ends when she cheats with Big. Though they reconnect later when Aidan opens a bar with Steve, Carrie calls off their engagement because she’s not ready. Despite Aidan marrying and having children, the duo shares a kiss in Sex and the City 2. Aidan is the anti-Big, and he doesn’t deserve the heartache that Carrie puts him through.
12 Patrick Casey
Carrie meets Patrick on the street in “Was It Good For You?” and reveals that his Alcoholics Anonymous sponsor suggests he not date anyone for a year. Ignoring that advice, Patrick trades his alcohol addiction for a sex addiction. When Carrie wants to take a break, Patrick relapses and strips on the street outside her home. It’s safe to say their romance didn’t last long.
11 Dr. Bradley Meego
Carrie is returning to her SATC self in And Just Like That, but it’s curious to see how she moves on following Big’s death. Carrie and Bradley have a summer romance after meeting at a book party, but Big is a major reason for their demise. Though Bradley is good on paper, after seeing Big with Natasha, Carrie completely forgets about the doctor. Perhaps Carrie and Bradley could’ve been something more if her feelings for Big weren’t so strong.
10 Bill Kelley
Carrie’s relationship with city comptroller Bill Kelley is idyllic, but quickly sours in the bedroom when Carrie refuses to act on Bill’s sexual kinks. Bill shames Carrie for being a sex columnist and their relationship fizzles. Bill should’ve considered Carrie’s professional before courting her and turning her into the perfect little political wife. It was never going to work between them.
9 Sean The Bisexual
And Just Like That is fixing Sex and the City’s biggest controversary with more representation. In what is perhaps Carrie’s biggest dating mistake, she basically shames Sean for being bisexual. Constantly asking him to compare her to men and asking if he prefers men more to woman, it’s no wonder they didn’t work out. Carrie leaves him at a party after a spin-the-bottle game. Carrie was never going to support her boyfriend’s preferences.
8 Wade Adams
Wade is a man-child who makes Carrie feel like she’s young again. As the owner of a comic book store, he rides a Razor scooter and still lives with his parents. Their brief romance ends after Wade’s parents catch them smoking pot in their home and Wade blames Carrie for bringing it. Wade cannot take responsibility for his actions and is barely an adult compared to Carrie. He may have made her feel young again, but Carrie doesn’t need to relive her youth.
7 Keith Travers
Shortly after Vince Vaugn’s role in The Lost World: Jurassic Park, he was portraying a lying celebrity assistant in Sex and the City season 3. While in Los Angeles, Keith convinces Carrie that he’s Matt Damon’s agent and shows her a lavish trip. Unfortunately, Keith turns out to be a liar and his romance with Carrie abruptly ends when they’re caught in bed at Carrie Fischer’s house after claiming he owns the property.
6 Ray King
Ray is the jazz owner who Carrie briefly dates in Sex and the City season 3. Though Carrie claims he’s the best she’s ever had in bed, she cannot overlook his ADHD diagnosis. Ray’s attention span is short, and he struggles to hold conversations with Carrie, not to mention his obsession with jazz. Instead of being understanding about his ADHD, Carrie breaks up with him.
5 Jack Berger
Berger seems like a good match for Carrie. He’s funny and a writer, but he has unresolved issues with his ex-girlfriend, and he becomes jealous of Carrie’s successful book deal when his own book deal is dropped. In what is Carrie’s real worst breakup, Berger breaks up with her on a Post-It note, saying he’s sorry and not to hate him. If Berger had more self-confidence, he and Carrie could have had a more successful relationship.
4 Howie Halberstein
When Carrie attends Charlotte and Harry’s wedding, she hooks up with the best man, Howie. Carrie is only looking for a rebound fling after her failed relationship with Berger, but gets more than she bargains for when she’s left hunched over after terrible sex with Howie. After trying to let him down and say she’s not actually interested, Howie gets drunk and trashes her in his best man speech.
3 Jeremy
X-Files has tons of famous guest stars, but star David Duchovny also guest stars on Sex and the City as Carrie’s high school sweetheart, Jeremy. Their romance is rekindled as Jeremy is funny and kind. However, Jeremy reveals that he checked himself into a psychiatric facility and Carrie even visits him in an attempt to continue their relationship. Carrie and Jeremy call it off when they realize it’s just not going to work.
2 Aleksandr Petrovsky
Carrie’s whirlwind romance with Russian artist Aleksandr Petrovsky leaves her feeling lonely. She moves to Paris to be with him, but finds herself constantly alone and no amount of grand, romantic gestures can change this. Aleksandr is inconsiderate of Carrie’s feelings and doesn’t seem to appreciate her. Their romance ends when Big comes to Paris to find Carrie.