The Worst Dates On ‘Sex And The City,’ Ranked

If you’re in the dating game long enough, you’re bound to go on a couple of duds. The odds of making a love connection every time are quite low, but even a mediocre date can be salvageable with the right attitude and enough cosmos. However, some dates are just impossible to save. The incompatibility goes beyond differing kinks or bad taste in restaurants. Some were only ever going to be complete and utter train wrecks.

On their quests for love and the perfect orgasm, the women of Sex and the City (which is available to stream anytime on HBO Now) managed to date some of the worst men in Manhattan. Sure, they eventually found guys like Steve (David Eigenberg) and Harry (Evan Handler), but the horrible dates they had to endure beforehand would leave anyone a little jaded. While dozens of men came and went out of the lives of the fabulous foursome, these were the particularly dreadful ones who were gone as quickly as they arrived.

10. Brad, The Worst Kisser Ever

There are a few ways to handle someone with an incompatible kissing style: grin and bear it, cut and run, or work together to find something that works for the both of you. Unfortunately for Charlotte (Kristin Davis), her season three date Brad (Ross Gibby) was not receptive to the idea that his technique could use some fine-tuning. It’s one thing to be a bad kisser; it’s another thing entirely to blame the other person for your own shortcomings. There is seriously such a thing as too much tongue, Brad.

9. Kevin, Mr. Prozac

Sometimes by taking care of one personal issue, you create another one altogether. This was the case with Charlotte’s season one date, Kevin (David Lee Russek), who traded in a sex addiction for giving up sex entirely. Kevin honestly needed to be in some intensive therapy for his problems, and yet he was content to pretend that they didn’t exist at all. Charlotte was looking for the whole package — marriage, passion, sex — so Kevin wasn’t going to cut it.

8. Vaughn Wysel, The Guy With The Great Family

Carrie’s (Sarah Jessica Parker) early days with Vaughn (Justin Theroux) were certainly promising. He was a fellow writer, so he understood the life on the page, and his family was a dream. However, his quick draw problems in bed proved to be a bridge too far. Like many dudes on this list, Vaughn could have benefited from a lot of therapy, but his first instinct to blame the women in his life for his problems was just an unappealing way to handle it. Maybe in another life Carrie and Vaughn could have made things work, but not in a reality devoid of personal responsibility.

7. Keith Travers, The Lying Assistant

The trip out to LA to shop her column to a film company didn’t go exactly as Carrie planned during season three, and her hookup with Keith Travers (Vince Vaughn) was no different. Not only did he lie to Carrie about his supposedly rich and fabulous lifestyle, but he passed off his employer’s home as his own. However, the truly unforgivable thing was the fact that he embarrassed Carrie in front of Carrie Fisher. For a writer, this is not something you can come back from.

6. Arthur, The Brawler

During their first season three date, Charlotte thought that Arthur (Brad Beyer) was truly something out of a fairy tale. He seemed like the shining white knight of New York, ready to defend Charlotte’s honor at the smallest slight, but it soon became clear that he was just looking for a fight. It had nothing to do with Charlotte at all, just Arthur’s fists. As nice as it would be to have someone in your corner, cleaning up his messes and apologizing to the wait staff after every dining room brawl would just be exhausting.

5. Ned, The Opportunistic Widower

It’s one thing to find love after tragically losing a partner. It is another thing entirely to leverage that loss into sex. Such was the case of Ned (Ken Deutsch), who Charlotte literally met at his wife’s grave in season two. By playing The Good Guy, Ned managed to get a date and then some from Charlotte, but it soon became clear that he was just looking get laid. And he was willing to exploit his dead wife’s memory in the process. Yikes.

4. Harvey Terkell, In Love With His Servant

Honestly, Samantha’s (Kim Cattrall) season two date Harvey Terkell (James McCauley) came with two red flags for the price of one. Not only did Harvey have a servant named Sum (Jina Oh) who was obviously in love with him and would take out her anger on Samantha, but Harvey always took Sum’s side, proving that he may have had some feelings for her as well. There were a lot of strange dynamics at play in this triangle, and none of them were worth the other perks.

3. Thomas John Anderson, The Repressed Playwright

Miranda easily had the most terrible luck with men on Sex and the City, and Thomas John Anderson (John Benjamin Hickey) in season one was easily one of the worst. The constant showering immediately after sex was manageable. Screaming at Miranda that they were both going to hell for having sex outside of marriage was not. The nuns really did a number on Thomas John, but at least he was able to channel it into his art. However, it left his relationship with Miranda with no chance of resurrection.

2. Jim, The Angry Ex

They say that you should never date someone who your friends hate, especially if it’s one of their exes, and never was that more true than with Miranda’s outing with Jim (Dominic Fumusa). Carrie warned her that Jim was not the nice guy that he seemed upon their meeting, but some mistakes have to be lived instead of just told. Not only did Jim harangue Carrie about their old relationship (about a decade in the past, get over it, dude), but he also turned on Miranda before the night was over. No one likes a cruel, petty man, so Jim was quickly placed on the relationship chopping block.

1. Kevin, The Bitter Coworker

One of Miranda’s season two dates, Kevin (David Lansbury) was a deeply angry dude whose bitterness about work spilled over into his relationship with Miranda. The restaurant was never good enough, Miranda was too happy, the cab driver was incompetent, the movie was too predictable… the list of grievances was never-ending. This was the kind of relationship that would choke the life out of someone, so it was only a matter of time before Miranda cut and ran. Life is too short for that kind of bullish*t. As nice as it is to have a date for Friday night, the better option is often cosmos with your best girlfriends to gossip about the Ones You Sent On Their Way.