Some of Carrie Bradshaw’s (Sarah Jessica Parker) most memorable romances in Carrie’s boyfriends in Sex and the City comprise much of the romance she experiences on the love-themed show. Still, her relationships with Aidan (John Corbett) and Mr. Big (Chris Noth) are not nearly as fun as the ones alongside “Power Lad” (Cane Peterson) or 20-something, tongue-pierced Sam (Timothy Olyphant).

Some of Carrie’s best flings are in the first few Sex and the City seasons, before the writer went back and forth between Aidan and Big. These were also before she met Jack Berger (Ron Livingston) or Alexander Petrovsky (Mikhail Baryshnikov). The sex columnist's more experimental flings within the first few season’s strong-themed episodes made for some fascinating insights. That said, some of the one-off romances had more promise than others.

10 Sean (Scott Rabinowitz)

Sex And The City Season 1, Episode 3, "Bay of Married Pigs"

Scott Rabinowitz appears as Sean in Sex and the City season 1, episode 3, “The Bay Of Married Pigs.” Carrie explores themes of monogamy in the episode as she finds herself dating the “marrying guy” after her married friends set her up on a surprise double date. Carrie and Sean date for a couple of weeks, and she calls him a DKNY dress because it’s not her style, but it’s “right there, so you try it on anyway.” Sean has his life together, but his desperation to settle down dominates the relationship.

Carrie ultimately ends it with Sean rather than opting to stay over because he “doesn’t fit.”

Sean has Carrie over for a housewarming party after he buys a classic six on the Upper West Side. When Sean gives Carrie a tour, he shows her a baby mobile he bought in Aspen in his office, which he says will be a nursery. Carrie ultimately ends it with Sean rather than opting to stay over because he “doesn’t fit.” While the relationship is blasé from start to finish, Sean’s romance helps to define how Carrie and her friends operate, making the fling memorable.

9 Kurt Harrington (Bill Sage)

Sex And The City Season 1, Episode 1, "Sex And The City"

Kurt Harrington isn’t a one-off fling for Carrie, but the former lover only appears once in Sex and the City, in one of the show's best installments. Bill Sage played the character in the self-titled Sex and the City season 1, episode 1. Carrie’s fling with Kurt helps define the series in its pilot episode when Carrie sees Kurt at the bar in the pilot while having drinks with Stanford. She calls Kurt a mistake she made when she was 26, 29, and 31, respectively, but upon seeing him again, Carrie embarks on a social experiment.

Carrie stages a run-in with Kurt, where they schedule a meet-up to rendezvous in the middle of the day. Carrie uses her experience with him to see if she can have sex like a man, which she describes as when “they have sex and then afterwards they feel nothing.” Ultimately, Carrie’s plan backfires when she sees Kurt later, and he tells her he loves the idea of having sex without commitment. The protagonist’s fling with Kurt is essential because it sets the tone for Carrie to explore her assumptions.

8 Patrick Casey (Richard Joseph Paul)

Sex And The City Season 2, Episode 16, "Was It Good for You"

Richard Joseph Paul appears as Patrick Casey in Sex and the City season 2, episode 16, “Was It Good for You.” Carrie meets Mr. Casey when he throws his cigarette into the street and accidentally hits the sex columnist in the arm. Patrick makes it up to Carrie by buying her a cappuccino, and Carrie learns that Patrick is a composer who writes music for the movies. Carrie and Patrick have a memorable cute meeting, and after enjoying a few cigarettes and cups of coffee, the writer gives the fellow smoker her number.

Carrie and Patrick see each other anyway, and after the pair makes love, as physical intimacy with her becomes his new vice.

Carrie is baffled when Patrick doesn’t call her but discovers it’s because he’s on a 12-step program, and his sponsor thinks he should wait a year to date. Carrie and Patrick see each other anyway, and after the pair makes love, as physical intimacy with her becomes his new vice. Ultimately, things end when Patrick tells Carrie he loves her prematurely. While Carrie and Patrick ultimately don’t work because Carrie doesn’t want to take on the relationship, the fling is the perfect romance for a single episode.

7 Wade Adams (Cane Peterson)

Sex And The City Season 3, Episode 15, "Hot Child in the City"

One of the best short-lived romances is Carrie’s brief fling with Wade Adams, aka “Power Lad,” in Sex and the City season 3, episode 5, “Hot Child in the City.” Carrie meets Wade at St. Mark’s Comics, where her shoe repair guy should be. Wade owns the comic book store and produces an amateur comic book called “Power Lad,” the nickname Carrie calls her new beau. When Carrie discovers that Wade lives in a classic six on the Upper East Side, she realizes he lives with his parents.

In a memorable Sex and the City ending, Wade blames Carrie for his marijuana mishap, and she subsequently takes Power Lad's stash.

Carrie finds Wade “fun” and “funny.” However, despite his terrace overlooking the park, Wade living with his parents proves to be an issue. After Wade and Carrie smoke Canadian supergrass while listening to records, Mrs. Adams comes home while the couple eats chicken wings. In a memorable Sex and the City ending, Wade blames Carrie for his marijuana mishap, and she subsequently takes Power Lad's stash. Despite being short-lived, Carrie’s fling with Wade is the perfect story.

6 Jeremiah (Samuel/Sam Ball)

Sex And The City Season 2, Episode 10, "The Caste System"

When she briefly spends time with Jeremiah (Samuel Ball) in Sex and the City season 2, episode 10, “The Caste Systems,” Carrie is also dating Mr. Big. Previously, when Big gives Carrie a Judith Leiber rhinestone clutch bag in the shape of a duck, she is so shocked that she tells her boyfriend she loves him. A few days later, Mr. Big still hasn’t returned the sentiment. Carrie gets upset at Big while attending a party on the Upper East Side, where she meets Jeremiah, a famous downtown performance artist and caterer, on the terrace.

Carrie notes that she and Jeremiah have flirted for years, and things take a turn when the performance artist shows her his new tattoo, partially located below his belt. Several things cause Carrie and Big to fight, and she eventually leaves the party with Jeremiah. They have margaritas, singing Three Dog Night’s “Joy to the World” as they walk the Manhattan streets back to Carrie’s apartment. Carrie blacks out, and despite waking up together, she and Jeremiah deduce they didn't sleep together. Jeremiah is cute and fun, but ultimately, it ends because Big finally tells Carrie he loves her.

5 Sam (Timothy Olyphant)

Sex And The City Season 1, Episode 4, "Valley of the Twenty-Something Guys"

Sex and the City season 1, episode 4, “The Valley of the Twenty-Something Guys,” includes another iconic one-off fling from the show’s first season. After she misses Big on their first date, Carrie meets Sam at the hottest new restaurant in Manhattan. Later, when Big shows up, Carrie examines Sam’s tongue piercing. When Big leaves shortly thereafter, frustratingly, Carrie follows Sam to a club where everyone is 20 years old. After sitting on his lap and drinking pony-necked beers, Carrie remarks that she and Sam kissed for five hours.

Carrie embarks on a short fling with Sam, who she likens to a designer drug.

Carrie embarks on a short fling with Sam, who she likens to a designer drug. When Carrie has another failed date with Mr. Big, she finds Sam at the club again and goes back with him to his apartment. Carrie wakes up the following day and is horrified by Sam’s filthy and chaotic New York loft, which the writer calls a "twenty-something apartment." Ultimately, Carrie decides she’s too old for Sam. Carrie just couldn’t deal with Sam's makeshift toilet paper coffee filter, understandably.

4 Jeremy (David Duchovny)

Sex And The City Season 6, Episode 10, "Boy, Interrupted"

Carrie rekindles an old flame in Sex and the City season 6, episode 10, “Boy, Interrupted,” when her high school sweetheart calls her for a reunion. Carrie notes that she used to make out with Jeremy in front of her locker, and she meets him for a drink and stays for dinner when she sees how cute and charming he still is. David Duchovny plays the former flame, who tells Carrie he’s taking a month to enjoy the country in Connecticut after spending the last decade working in Denver.

He notes that he’s sorting through some things, and when Carrie invites him over for a movie and wants him to stay over, Jeremy its he checked into a psychiatric facility called Juno-Spears. While Jeremy initially says he’s just doing some soul-searching, he reveals later that he plans to spend the next eight to 10 months at the institution. Carrie and Jeremy ultimately agree that they are in different places in their lives and break off the relationship, but seeing her with her high school sweetie is a fun change.

3 Yankee Joe/Joe Stark (Mark Devine)

Sex And The City Season 2, Episode 1, "Take Me Out to the Ballgame"

Carrie dates a Yankee in Sex and the City season 2, episode 1, “Take Me Out to the Ballgame.” Carrie is brokenhearted in the premiere after breaking up with Mr. Big in the season 1 finale. When her friends surprise her by taking her to a baseball game, Carrie catches a fly ball and uses her press to get it signed by the new Yankee, Joe Stark (Mark Devine). Having had a few beers, Carrie invites Joe to an Dolce & Gabbana party.

After Carrie and Joe show up on Page Six after their first date, they have a better time on their second one, but Mr. Big shows up at the bar where they’re drinking.

While Carrie rebounds with the new Yankee, she keeps mistaking strangers for her ex, showing how difficult her breakup is. After Carrie and Joe show up on Page Six after their first date, they have a better time on their second one, but Mr. Big shows up at the bar where they’re drinking. Despite having fun plans ahead, Carrie cries into Joe’s mouth while she is kissing him after her encounter with Big and begs him to leave her alone, ending a stellar fling due to not being ready to date.

2 Sean (Eddie Cahill)

Sex And The City Season 3, Episode 4, “Boy, Girl, Boy, Girl …”

Carrie dates Sean (Eddie Cahill) in Sex and the City season 3, episode 4, “Boy, Girl, Boy, Girl …” Carrie calls Sean her “generation something-else date” who she met at a downtown party celebrating a new internet magazine that Sean runs. He takes Carrie ice skating, and after she says she doesn’t believe it’s a date without cocktails, Sean proves he is the writer’s perfect match when he reveals that he has a flask of Jim Beam. Carrie calls Sean sexy and charming. However, when they discuss past relationships, Sean’s bisexuality throws Carrie off.

Carrie reaches her limitations with Sean's sex and gender-positive environment when the group plays spin the bottle, and Carrie kisses Sean’s friend Dawn (Alanis Morissette).

When Sean takes Carrie to a club called Hair, she thinks that Sean is checking out other men. Despite sleeping with Sean and having a great time, the harsh reality of rewatching Sex and the City season 3 is that Carrie is so distracted by how she compares with Sean’s male lovers that she misses out on great moments. When Sean takes Carrie to a party at his ex-boyfriend’s place, she reaches her limitations with Sean's sex and gender-positive environment when the group plays spin the bottle, and Carrie kisses Sean’s friend Dawn (Alanis Morissette).

1 Ben (Ian Kahn)

Sex And The City Season 2, Episode 3, "The Freak Show"

In Sex and the City season 2, episode 3, “The Freak Show,” Carrie meets Ben (Ian Kahn) at a fountain in the park, where he reads a book. Ben strikes up a conversation, and despite not having dated in two years, he asks Carrie out to dinner. On their outing, Carrie learns that Ben is the editor of a hip political magazine, and she remarks that Ben makes her laugh. Despite sharing a perfect first kiss, Carrie doubts the relationship after setting Miranda (Cynthia Nixon) up with one of Ben’s friends, discovering he’s the “Manhattan Guy.”

Carrie defines the "Manhattan Guy" as "A genetically mutant strain of single men that fed on Zabar's... and midnight shows at the Angelica."

Cynical Miranda tells Carrie that if Ben’s friend is a “freak,” then he probably is, too. Then, Carrie spends the night at Ben’s place, and he leaves her alone the following day. The columnist rifles through her beau's things, looking for something weird. When Ben comes home early, he finds Carrie struggling to get into a locked box, convinced he’s hiding something, but Ben reveals it’s just his Cub Scout badge collection. Ben is an excellent match for Carrie, but unfortunately, she leaves his apartment after the mishap, and they never see each other again in Sex and the City.