Sex and the City premiered on HBO on June 6, 1998. That’s 20 years ago today! How has it possibly been that long? It’s no secret that I’m a big fan of the show and that its cosmopolitan fairytale influenced my own romance with NYC. Before moving to NYC (10 years ago, I’m exactly 1 decade younger), I tried to convince myself the reality would be nothing like the show. I wanted to be realistic (like Miranda) and not set myself up for failure.

The funny thing is, much of the show is very much based on actual New York City life. In the past ten years I’ve many moments that made me think, “this is like an episode of Sex and the City!” In honor of the 20th anniversary, below are 20 such stories.

Moments My Life Felt Like An Episode of Sex and the City

Season 1

1. One of the very first episodes of Sex and the City is all about models and the men who “modelize” them. Models are a total NYC phenomenon, you can spot them in “the wild”. I found many of the stereotypes portrayed in this episode to be true when I was the one “brand ambassador” leading a team of 4 bitchy high-fashion models. Models: Beauty on the Outside, Bitchy on the Inside

2. Season 1 has all the ladies dating younger 20-something men in an episode so titled “Valley of the 20Something Guys”. Shortly after I turned 30, I dated a guy who was still in his 20s and he spent way too long on the date moaning to me about turning 30. That full story is: Dating Younger Men Who Bemoan “Pushing 30”

Season 2

3. Sex and the City popularized the term “fuck buddy”. In this Season 2 episode we see that Carrie, Samantha, and Miranda all have such a pal they really only see for sex. Sam calls it “dial-a-dick”. This is as close as the show gets to discussing booty calls. The closest I got to a booty call was when my friend Josh called me at 2pm with a proposition. Full story: I Get Booty Calls at 2PM on Sunday Afternoons

4. In Season 2, “The Man, the Myth, and the Viagra”, Miranda goes on a date to a stand-up comedy club. Her date goes to the bathroom, and the comic proceeds to eviscerate her in a totally humiliating way. When I went on a 3rd date to a stand up comedy, the comics made my date and I repeatedly feel soooo awkward. That full story is:  Don’t Take Your Third Date to a Stand Up Comedy Club

5. Who can forget Carrie’s disastrous “Single and Fabulous?” interview (and cover shot) with New York magazine? I had a somewhat less disastrous interview with Time Out New York magazine after they set me up on a date for their Undateables series. That full story is: Time Out New York Undateables: Super Sweet VS Cruelly Candid?

6. Carrie says “I love you” for this first time when Big gives her ducking ugly purse. I said “I love you” for the first time when my boyfriend (not me!!) was tripping on acid. That full story is: Sometimes It’s a Long Trip to “I Love You”

7. In the last episode of Season 2, Samantha meets the memorable “Mr. Cocky” who picks her up literally on the street. I also got picked up by a guy a met on the Manhattan streets, and it made a pretty great story too:  I Say Yes to Day Drinking During a Work Day

Season 3

8. Remember that episode (“What Goes Around Comes Around” Season 3) when Carrie gets robbed, down to her Manolos? It made me feel a little better when I myself got robbed on the NYC streets! That full story is: I Got Robbed on the Streets of New York City (Part 1)

9. One of my favorite episodes ever, Season 3 “The Freak Show”, Carrie gets picked up by a cute guy while sitting on the side of a fountain in Central Park. His name is Ben, he’s pretty much perfect, his most freaky flaw is a sweet Tweety Bird tattoo. My very first day in Manhattan, I got picked up in Central Park, by a guy who would later get giant “No Shame No Regret”  tattoos on his arms. That full story is Picked Up on a Park Bench

10. Season 3 “No Ifs, Ands, or Butts”, Charlotte dates a terrible kisser. When I dated a terrible kisser, I was totally comforted by this episode. My guy’s problem however, was not too much tongue. That full story is His Kiss Felt Like a Dementor’s

Season 4

11. Carrie memorably walks the catwalk for a runway show in Season 4. When I worked backstage for the final runway show of New York Fashion Week as a model dresser, I couldn’t help but think of this episode! That full story is: Backstage for the Final Runway Show of New York Fashion Week

Season 5

12. The first episode of Season 5 was all about Fleet Week in NYC. Every Fleet Week there are actually sailors all over NYC, just like the show said there would be. You can’t help but think of Sex and the City that week! Full story is: The Fantastic Allure of a Man in Uniform: Fleet Week NYC

Season 6

13. Ever since Carrie Bradshaw got called for jury duty in Season 6, being summoned in NYC got a little better! “It’s just like Sex and the City”, I thought, as I enter the courthouse. That full story is: Jazzed About Serving New York City Jury Duty? You Crazy?

14. The show’s most memorable break up might be in Season 6 when Berger leaves Carrie nothing but a post-it note. After Donald Trump was elected, his entire home town of New York City felt the need to try to break up with him via post-its. That full story is A Post-it For Your Thoughts? NYC Subway Therapy

Full Series

15. I saw Sarah Jessica Parker who plays Carrie Bradshaw shopping at CVS in sweat pants on a Friday night. It totally felt like she was filming Sex and the City 3 and I was an extra. The full story is: New York Cliché of the Day: Sarah Jessica Parker Celebrity Sighting

16. This is never mentioned on the show, but as a sex writer, Carrie must have had guys who wanted to date her just from reading her column. That kind of happened to me from writing this blog! That full story is: The Most Intriguing Online Dating Message Ever

17. Throughout the show, the foursome goes to many art openings at the gallery where Charlotte works. Some of them are a little ridiculous, like the one featuring a painting of Charlotte’s c*nt or her best attempt at drag. The first Chelsea art gallery opening I ever attended was pretty bizarre too. That full story is A Chelsea Art Gallery Opening Indistinguishable from Sailor Moon on Drugs

18. Meeting men in all sorts of different places happens all the time on the show. This isn’t a total fantasy! It does happen in New York with some frequency (or at least it did pre dating apps domination). I even met a guy while thrift shopping once. The full story of that is: The Man I Met at Goodwill

19. All four ladies on Sex and the City are forever dating men who kind of suck. A vast array commitmentphobes, weirdos, snobs, etc who are so clearly wrong for them. I certainly dated my fair share of duds like that, this guy was one of the worst: Shitty Date Story: Misery Loves Company and Wine Snobs

20. Who could count how many break ups happened on Sex and the City? The show definitely helped me through my first, so much so that I could almost hear Carrie’s voice over while it was happening to me. That full story is: My Life as a Chick Lit Blurb

Do you have any stories that felt straight out of Sex and the City? I’d love to hear them, feel free to share in a comment or link!