Our Ultimate Ranking of Sex and the City’s Most Important Relationships

We couldn’t help but wonder how time sure does flies.

It’s been more than 20 years since we first met the ladies of Sex and the City in June of 1998, meaning it’s been more than 20 years since we first started debating their many relationships.

Carrie (Sarah Jessica Parker) and Big’s (Chris Noth) epic tale of love and giant closets may have dominated much of the conversation, but they weren’t the groundbreaking HBO series’ only worthwhile love story. 

We fell for Charlotte (Kristin Davis) and Harry (Evan Handler) plus Miranda (Cynthia Nixon) and Steve (David Eigenberg). And had some thoughts about Carrie and Berger (Ron Livingston)…and Carrie and Aleksandr Petrovsky (Mikhail Baryshnikov). Then there was Samantha (Kim Cattrall), with her exciting dalliances and jaw-dropping stories of bed hopping. But her affair with Smith Jerrod (Jason Lewis) will always hold a special place in the hearts of fans for many reasons.

Now, take a trip down memory lane with our ultimate ranking of the show’s 15 most important relationships, starting with one we may all prefer to forget and ending with one iconic one that may or may not surprise you. 

There was a lot of sex on Sex and the City, but even more love.

Throughout the years, Carrie, Miranda, Charlotte and Samantha each dated their fair share of guys and sometimes gals, kissing and telling over many cosmos and lunches. But setting aside every one-episoe love interest, there were 15 relationships on the show that really made an impact…and that we can still remember 20 years later. 

So which Sex and the City relationship ranks as the HBO series’ all-time best? Our pick for No. 1 may just surprise you…

Ugh, what an asshole.

Best moment: N/A.

It’s hard to remember the couple’s early banter-filled cute moments after all the horrible, passive-aggressive crap the writer pulled on her later on. HE BROKE UP WITH HER ON A POST-IT.

Best moment: None are coming to mind at the moment, Berger. We’re sorry, we can’t. Don’t hate us.

No one believed this relationship would last, right? Still, Samantha gave it the ol’ college try. 

Best moment: After Samantha told Big to “back off” during a night out with Carrie, her new beau and Maria, Maria told Samantha she couldn’t be just friends. 

Oh, the Russian. Their relationship started off too romantic to be true…and it was. He didn’t get along with her friends and Carrie’s impulsive move to Paris proved to be a disaster.

Best moment: After too many grand romantic gestures, Carrie fainted. So naturally, Petrovsky took her, in her dream ballgown, to McDonald’s, where they slow-danced while waiting for fries.

On paper, Trey was the perfect guy for Charlotte. But the cracks began to show (overbearing mother, “Trey can’t get it up,” not wanting kids, etc.) soon after their wedding. Also: he gave her a cardboard cut-out baby. Who does that?!

Best moment: When Trey took Charlotte to Tiffany’s so she could pick out her dream ring to make up for the infamous “Alrighty!” comment.

The first relationship Samantha had that was based on sex came to an end because of, well, sex. It was James’ small penis, to be exact. 

Best moment: When Samantha told James she loved him. A huge (no pun intended) moment for her.

Poor, poor Skipper. He was kind of like a Steve-lite, and Miranda was able to walk all over him.

Best moment: When he calls her “luminous” when they run into each other at a bodega.

Sure, it came out of nowhere in the movies that Carrie’s BFF and Charlotte’s wedding planner-turned-bestie would get together, but it kind of works for us.

Best moment: In their wedding vows, when Anthony said, “It wasn’t love at first sight, but it turns out it was love. You are the first man to accept me for the man that I actually am.”

Let’s face it, Aidan was a great guy but he wasn’t The Guy for Carrie…no matter how hard they both tried to convince themselves that he was. 

Best moment: Is it weird that we loved their breakup scene, the second one, where they slept on the floor of the apartment they would never live in together?

Talk about a catch. Robert was almost perfect: he was a hot doctor for the New York Knicks who watched the same soaps as Miranda. His one flaw? He just wasn’t Steve.

Best moment: Their first kiss at their “lockers,” (i.e.: mailboxes). Or her taking a personal day for the first time ever for him. OR THE CHICKEN POX.

Of all the guys on SATC, Smith Jerrod might just be the best. He was so patient and so giving with the wild Samantha, who fought tooth and nail not to fall in love with the model-turned-superstar. 

Best moment: Who doesn’t tear up just thinking about Smith shaving his golden locks for Samantha when she lost her hair while undergoing chemo? 

Absof–kinglutely.

Best moment: Come on, how can we not choose Big going to Paris to finally tell Carrie she’s the one? (Although the fart-in-bed/whoopee cushion prank still makes us smile.)

They say love often finds you when you least expect it…like when your sweaty schlub of a divorce lawyer turns out to be the man of your dreams and the best father to your children you could’ve imagined.

Best moment: Their mess-filled, imperfectly perfect nuptials. From the beginning of the series, Charlotte wanted the fairy tale wedding, but what she got was the fairy tale marriage.

Just like Miranda’s feelings for Steve snuck up on her, our love for this couple hit us like a ton of bricks. 

Best moment: If any moment perfectly represents SATC‘s most low-maintenance couple, it was Miranda’s out of nowhere proposal and their super low-key wedding in the park. So them.  So perfect.

“The most important thing in life is your family. There are days you love them and others you don’t, but in the end they’re the people you always come home to. Sometimes it’s the family you’re born into. And sometimes it’s the one you make for yourself.”

Best moment: We were SO tempted to choose Carrie walking Miranda down the aisle at her mother’s funeral, but we thought a moment with all four girls was appropriate. Our choice? When Miranda doesn’t give two shits about her wedding after hearing about Samantha’s breast cancer diagnosis, with all four girls tuning out the celebration to just be together. Because that’s what friendship is: putting others before yourself. 

(This story was previously published on Wednesday, June 6, 2018 at 3 a.m. PT)