Sex And The City Carries 10 Worst Flings Ranked

Sex And The City: Carrie’s 10 Worst Flings, Ranked

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Carrie dates her fair share of duds throughout Sex and the City’s run, and while some men show potential at first, others are wrong straight away.

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Sex And The City Carries 10 Worst Flings Ranked

For six seasons, the ladies of Sex and the City provided their fans with complex relationships, laughs, heartbreak, and some really good fashion choices. It also provided some of the best scenes that will live rent-free in fans’ heads for years to come, and while some involve the best relationships in the series, there are others that feature some of Carrie Bradshaw’s more questionable flings.

Some of the best episodes involve these Mr. Wrongs, and the situations Carrie Bradshaw (Sarah Jessica Parker) gets into with them. Everyone has their own quirks, but these guys are on a whole different level.

10 “The Man Who Steals Cheap Used Books For No Reason”: Season 2, Episode 3

Sex And The City Carries 10 Worst Flings Ranked

Carrie Bradshaw has had a lot of dates through the Sex and the City series, but in the episode, “The Freak Show,” she ponders the idea that all men in the city might be “freaks.” Carrie goes on a trio of dates throughout the episode, and one of them happens to be a perfectly capable man who decides to steal things for the sake of it. This might be giving insight into a deeper issue and Carrie catches wind of it.

She decides that everyone might have a little “freak” in them after she goes through another date’s apartment looking for a flaw that isn’t there.

9 Willie Applegate: Season 6, Episode 1

Sex And The City Carries 10 Worst Flings Ranked

Even though Carrie has a date with fellow writer, Jack Berger, she tries her hand at dating “simultaneously,” after getting advice from the girls. She meets Willie Applegate, played by Wallace Langham, a seemingly nice man, but his nerves and obsession with a possible stye in his eye have him acting extremely awkward.

What follows is a string of uncomfortable events, such as Wallace getting balsamic vinegar in his eye and a pigeon landing on his head. It’s safe to say this is one of Carrie’s clumsiest dates. At this point, Carrie might be better off dating someone who she really wants to date, instead of putting herself out there just so she can date multiple people at the same time.

8 Gilles: Season 1, Episode 5

Sex And The City Carries 10 Worst Flings Ranked

While doing a bit of cardio, also known as “shopping” for Carrie, she runs into her friend Amalita and her new boyfriend. Amalita’s life is extravagant with trips and rich men, and while she’s in town, she invites her to dinner. Later on, Carrie meets an architect named Gillies, who she is immediately attracted to. She decides to spend the night with him at his hotel, and after a fun-filled night, she wakes up to find Gilles has left and a stack of money is left instead.

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Apparently, Amalita is a sex worker and Gilles assumed that Carrie was too. It might’ve been a miscommunication, but it was still incredibly shocking for Carrie to wake up to that.

7 “The Man With Two Faces”: Season 2, Episode 3

Sex And The City Carries 10 Worst Flings Ranked

Going back to the episode, “The Freak Show,” Carrie’s Date #2 (James Joseph O’Neil) seemed like a nice guy who is into Carrie, but one wrong move and it sets the guy off, which isn’t a good sign.

Carrie gets her first and last taste of this when they are in line waiting for the movie. When Date #2 feels like the man behind him is listening in on their conversation, he loses his cool. Everyone has bad days, but this might a road that Carrie doesn’t want to go down.

6 Howie Halberstein: Season 6, Episode 8

Sex And The City Carries 10 Worst Flings Ranked

Weddings are the place for singles to mingle with each other, and perhaps, find love themselves. Unfortunately for Carrie, this wasn’t her day. While her friend Charlotte (Kristin Davis), is getting ready to marry her second husband, Carrie meets Howie Halberstein (Bryan Callen).

After Howie and Carrie get more acquainted after the rehearsal dinner, things don’t quite go to plan. Howie’s intimacy skills are way too fast for Carrie, and she ends up hurting her back. At the wedding the next day, Carrie breaks it to Howie that she isn’t that interested, and Howie doesn’t take it well. After shooting daggers at her all day with his eyes, Carrie realized she dodged a bullet … but not fast enough.

5 Ray King – Season 4, Episode 3

Sex And The City Carries 10 Worst Flings Ranked

On a friendly outing with Mr. Big (Chris Noth), Carrie catches the eye of jazz musician Ray King (Craig Bierko). Even though Mr. Big tries to intervene, Carrie and Ray end up having a short romance. Ray is nice enough and he and Carrie have intense chemistry, but that’s about it.

They have nothing in common with each other, and his attention span was everywhere and anywhere, which means the relationship could never last or go anywhere serious. This one was a bummer because there was potential for Carrie to finally leave her messy relationship with Big behind for good.

4 Wade Adams: Season 3, Episode 15

Sex And The City Carries 10 Worst Flings Ranked

The women of Sex and the City have been known to date their fair share of men (and women) their age or older, and when Carrie becomes interested in Wade Adams (Cane Peterson), also known as “Superboy,” her interest shifts to younger men. Carrie doesn’t mind because she wants a fun-filled romance with the comic bookstore worker, which entails buzzing around New York City and even partaking in a little marijuana.

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Carrie finds out that Wade lives with his parents, and when they get caught by his mother with the marijuana, Wade shows his age by blaming Carrie for bringing it. Maybe feeling young again isn’t all that it’s hyped up to be, and while Carrie had to move on from Wade, she did decide to take “her” marijuana with her, which can be considered grade-A karma.

3 Keith Travers: Season 3, Episode 14

Sex And The City Carries 10 Worst Flings Ranked

Vince Vaughn is known for his comedic roles in movies, such as Wedding Crashers and Couples Retreat, but before all of that, he guest-starred in the episode “Sex and Another City.” Vince played Keith Travers, a man Carrie meets in Los Angeles, after traveling there with the girls. Keith sweeps Carrie off her feet after being rejected from entering a movie premiere after-party, and telling her he’s Matt Damon’s agent.

Of course, Keith is not all that he seems, and as he and Carrie hang out at his “mansion,” the real owner, Carrie Fisher, breaks up their party and reveals his real identity. Keith is housesitting for her and has lied his way into Carrie’s arms. Ouch. Even though the fling didn’t work out, it was one of the better Sex and the City episodes that wasn’t set in New York City.

2 Seth Robinson: Season 2, Episode 13

Sex And The City Carries 10 Worst Flings Ranked

It’s always interesting when a musician transitions over to the acting world, and when Jon Bon Jovi decided to jump on an episode of Sex and the City as a guest star, it was questionable, to say the least. But it wasn’t that the “Living on a Prayer” singer didn’t pull it off, but more what his character did that was the issue.

As Carrie continues to get over her break-up from Mr. Big, her friends recommend therapy because she clearly isn’t getting any better. In the waiting room, she meets Seth Robinson, played by Jon Bon Jovi. At first, Seth seems like the perfect match, but when he tells Carrie he dumps girls after they get intimate, she immediately realizes this is not the guy to settle down with. In this Sex and the City dating mishap, Carrie could have used a bit of Miranda’s tough-love advice.

1 Bill Kelley: Season 3, Episode 2

Carrie and the girls take a visit to Staten Island in the episode, “Where There’s Smoke…” where Carrie is on the jury to judge the New York Fire Department’s annual male calendar finalists. While judging, she meets Bill Kelley, played by John Slattery. He seems like the perfect catch: he’s good-looking, rich, and attracted to Carrie.

After weeks of the relationship going well, he finally asks her for a sexual favor that has her thinking twice. The request leaves Carrie speechless and unable to commit. For such a great catch, this was a terrible letdown for her.

Link Source : https://screenrant.com/satc-carrie-worst-dates/

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