HBO's Sex and the City is a show about four female friends in their thirties who live in New York City and they mostly have just one thing on their mind: men. Their relationship with love is sometimes a bit unhealthy, but they do make for an endearing friend group. They each look for different things when it comes to their ideal partner and they never seem to get tired of meeting new people and going on dates, even though most of them don't work out.
Sex and the City offered insight into the harsh realities of the dating world, which is summed up in the show's best quotes about dating. Most of the men were introduced after the women went on several dates off-screen, but sometimes, fans were lucky enough to see our beloved ladies navigate their ways through some pretty bad, and sometimes hilarious, first dates.
10 Wade ("Hot Child in the City")
When Carrie met the aspiring comic book creator while looking for a place that used to fix her shoes, they instantly hit it off. He gave her a copy of his very own comic book called "Power Lad", which later on led to their first date.
Despite going to the arcades, a place that Carrie didn't seem to care that much at all about, the two had quite a good first date. It was all ruined when they came to his fancy flat in the Upper East Side. It turned out that he still lived with his parents and Carrie even had to go through the awkwardness of meeting his mom, Mrs. Adams.
9 Ray King ("Defining Moments)
Carrie's dates are typically ruined by weird circumstances rather than her poor choice in men. At this point, Carrie and Big were just friends and they went out to a jazz club where Carrie instantly locked eyes with the charismatic bar owner. They instantly hit it off, but Big wouldn't get lost.
Carrie and Ray went on to go on a date without Big as a chaperone, but they ran into each other yet again at the restaurant. What are the chances? Nothing ruins a first date like your emotionally unavailable ex-boyfriend who is suddenly acting all possessive.
8 Jim ("Frenemies)
Miranda had her fair share of romantic interests, much of which were just outright bad. In "Frenemies," Carrie and Miranda went to a wake of a stranger Miranda was supposed to go on a date with.
There, Carrie ran into her ex, Jim. Because he was cynical like Miranda, they hit it off. It's pretty bad that they had to arrange a date at a wake, but it only got worse when it turned out that Carrie was right and that he was an absolute a**hole.
7 Aleksandr Petrovsky ("The One")
Aleksandr Petrovsky seemed like a pretty interesting man, but his first date with Carrie was an absolute nightmare. The dinner party started at 1 AM and Aleksandr greeted Carrie by telling her she was late. Carrie tried her best to seduce him with her witty banter, but the only thing he noticed was that she wasn't pronouncing his name right.
Additionally, he didn't seem to be interested at all in what she does, while he also left her hanging every time she tried to initiate a new conversation topic. It makes no sense that Carrie was willing to move overseas for this self-absorbed man.
6 Tom ("Cover Girl")
Miranda met Tom at the Weight Watchers where she was trying to get rid of her baby weight. They bonded over glazed donuts. As Tom suggested they should also score some activity points, the date ended in Miranda's bed with fireworks. The date was instantly ruined when it turned out that Tom, as Carrie put it, is "an overeater and he overate her".
Needless to say, Sex and the City didn't age that well. So what if the guy had Miranda "all over his face." This shouldn't constitute a bad date, but it certainly was for Miranda.
5 Harry ("The Big Journey")
Charlotte's husband Harry turned out to be the best man in the entire series, but that doesn't mean that their first date was magical as well. Charlotte only decided to hire Harry as her divorce attorney because she thought he was ugly and had bad manners. When he delivered the papers to her place, he was sweating all over them. Fans all felt bad for Harry at this point, but he luckily managed to marry the woman of his dreams in the end.
Charlotte wanted to use him as rebound and his bachelor pad definitely gave off some seriously cringy vibes - especially because of the tacky zebra carpet. Well, the bad date turned into a great one after Harry told Charlotte that he thinks that she's the sexiest woman he ever met and proclaimed himself a "f*cking Romeo."
4 Mr. Big ("Valley Of The Twenty-Something Guys")
In season 1, Carrie and Big were yet to call one of their get-togethers a date. Their first date was pretty bad. First of all, Big called it a "drink thing" and he showed up late. Carrie didn't let that ruin her night and she eventually found herself flirting with a guy with a pierced tongue. Big then showed up just to tell her that he waited and looked for her for so long that he actually ran out of time.
Carrie thought he was "tricky and complicated," but there was nothing tricky going on here, he was simply showing her his true nature. He is a commitment-phobe who only messes with her head and his behavior would certainly not fly today.
3 Adam Ball ("Easy Come, Easy Go")
No Sex and the City list is complete without an honorable mention of Samantha Jones who won at life even when it comes to dating. She wasn't the dating type at all and usually didn't wait until letting a man into her bed. In season 3, she found herself dating Adam, a man who "tasted" a bit strange.
Needless to say, Samantha wasn't too thrilled about a first date that left her with a bad taste in her mouth. Needless to say, he didn't stick around long.
2 Ethan ("The Cheating Curve")
In "The Cheating Curve", Miranda found herself on the first date with Ethan, a man who was passionate about documentaries. They first saw a four-hour-long documentary, and Miranda had to kiss him just to shut him up since he wouldn't shut up about it.
When they made it to his place, it turned out that Ethan likes to watch porn while having sex. Miranda gave him a chance anyway, but in the end, he chose the ladies from the video over her.
1 Arthur ("Where There's Smoke")
Arthur seemed to have it all: he was charming, well-mannered, successful and he went to Harvard. Charlotte was smitten, especially when he said he wants to have "the perfect marriage".
But what good are his marital goals when he clearly has anger management issues? When a stranger bumped into Charlotte's chair, Arthur went on to punch the guy in the face because that was no way to treat a lady. This encounter must have been so embarrassing for poor agreeable Charlotte.
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