Carrie Miranda, Samantha, and Charlotte all did their fair share of dating while living in the Big Apple. The fashionable friends on Sex and the City always had a new man in their lives, whether it was only for a day or for some, life. It is safe to say that some of these guys ended up as total winners. Charlotte's lawyer beau-turned husband, Harry, was an absolute gem of a man. Samantha's younger lover, Smith Jerrod, didn't last forever, but he was great to her during their time together. Even Mr. Big came around (after a million years of being a dud).
While some of the guys turned out to be keepers, others were fellows that the ladies would probably like to erase from their memories. Of all the men (and women) that the gals tried on for size, these are the 10 most questionable ones, by far. You win some, and you lose some ladies!
Nick Waxler
Remember when Miranda hooked up with the sports agent, Nick Waxler? The name might not ring a bell, but the incident likely will with true fans of the show.
While out with Nick, Miranda learns that he has a steadfast rule about only dating models. Miranda was only invited out with him as a request by his friends, who are bored with the far-from-intellectual dates he typically brings. Miranda was not impressed at the reason behind the disastrous first date.
Joseph Adler
After Miranda discovers some unsettling reproductive news, she heads out on a date with one Joseph Adler. Miranda has had some questionable dates in her lifetime, and this guy ranks up there with the worst of them. While Miranda is trying to overcome the news about her health, she has to sit and hear all about this guy's hair plugs - not very romantic.
Miranda opens up to him about her reproductive issues and he basically makes her feel even worse. She comments on his beloved plugs, and from there, the date is DOA.
Vaughn Wysel
At first, it looks like Vaughn and Carrie might really have a chance at happiness. They are both writers, both good looking, and Carrie instantly falls for his family, as they fall for her as well. This one turned out to be too good to be true, however.
Vaughn came with all sorts of mommy issues and emotional baggage that was anything but attractive. Carrie caught on to his emotional deficits and took off running for the hills - probably a good decision, in the end.
"Worst Kisser Ever" Brad
Charlotte met Brad in season three, and sparks flew. They seemed to get on well enough until Brad opened his mouth and failed Kissing 101.
Charlotte's suggestions on how to better his game didn't go over well and her date appeared too wounded to carry on. He lashed out and blamed Charlotte for their bum luck in the smooching department. Taking things past a handshake in this situation proved ill-fated for all involved.
Harvey Terkell
Samantha rarely backs down from a challenge, especially when it concerns men. She had her work cut out for her in season two when she tried dating a gentleman named Harvey Terkell. Terkell was more interested in his servant, Sum, than he seemed in Sam.
Sum appeared to return his affections, making for some really awkward moments. When Samantha tried to tell Harvey how the staff was treating her, Harvey immediately took Sum's side, sending a message loud and clear: there was only going to be one woman in his life, and it wouldn't be Samantha.
Keith Travers
In season three of the hit series, Carrie heads out to sunny and warm Los Angeles to sell her column to the film industry. There she meets and hooks up with a guy named Keith, played by Vince Vaughn.
Keith wines and dines Carrie, making her think he lives among the rich and famous. But Carrie and the viewers soon learn that he is only posing as a rich and successful guy, pretending his employer's home is his own. He doubles down in the bad date department when he embarrasses Carrie in front of the esteemed Carrie Fisher. This one was a total fail.
Trey MacDougal
Charlotte spent years on a mission to find a wealthy, uptown husband, one of her sadder traits, until she transformed into an entirely different woman. Trey ended up as Charlotte's first husband, and on paper, he seemed pretty perfect for her. In real life, he was questionable, at best, and they didn't work together. Furthermore, he had such deep devotion to his uppity mother that it became crystal clear that Charlotte would always be playing second fiddle to the OG Mrs. MacDougal.
Charlotte and Trey eventually divorced, making way for Harry Goldenblatt, Charlotte's lawyer, to swoop in and show her what true love really looked like.
Aleksandr Petrovsky
As soon as Carrie laid eyes on the famous artist, fans started questioning how far this would go. Everyone kept waiting for Carrie to break it off with the sometimes physically and emotionally unavailable eccentric guy, but instead, she ran off to Paris with him.
Everything went downhill at warp speed once Carrie landed on French soil. The relationship ended with a bang, and viewers couldn't help but think, "Girl, we knew this was coming."
Mr. Big
Fans of the show know that when all was said and done, Carrie and Mr. Big DID indeed end up together, not before everyone questioned why Carrie could not let this man go. For years, these two proved to be about as toxic as possible. They hurt one another, cheated on their partners with each other, and broke up more times than fans could count.
Every time their worlds collided, viewers thought, "Oh no, not again!" Fans continued to question Carrie's decision to love Big all the way to the bitter end and maybe still do.
Richard Wright
Samantha doesn't get emotionally wounded often, but one guy managed to shatter her heart into a thousand pieces. Richard Wright was the hotel giant who made Samantha feel like a princess.
But Samantha started to feel like Richard was stepping out on her, and fans questioned her blindness to Richards's ways. It was pretty obvious that Samantha was not his only lady and she did end up catching Richard in the act, confirming that this guy was no good.