TV Romance
‘Sex and the City’: The 7 Worst Boyfriends of All Time, Ranked
Sex and the City, the show that keeps on giving. She continues to teach us lessons over 16 years later (and still going strong), and one of the main lessons, one could argue, would be identifying which men you absolutely should not be dating. Lucky for us, Carrie (Sarah Jessica Parker), Miranda (Cynthia Nixon), Samantha (Kim Cattrall), and Charlotte (Kristin Davis) date them so we don’t have to.
Over the course of 94 episodes, there were plenty of duds that the girls had to parse through. One of the strongest features of this show was how each relationship functioned so differently. Sometimes, the men were just a good lay. Sometimes, they were the only option at a wedding’s singles table. Other times, they were the handsome stranger you ran into on the street, on an elevator, in your therapist’s office…Well, Carrie should have seen that one coming.
And as Carrie so aptly put it herself, most of the guys they dated were freaks. Many of the characters didn’t even make it into serious relationship territory, but of the ones that did, there was still plenty of havoc wreaked on the lives of our four favorite socialites, except for Harry (Evan Handler) and Steve (David Eigenberg), who will never do any wrong in my mind.
Keep reading to see if you agree with our list, and comment below if we missed any of your least favorite boyfriends from the series.
7. Jack Berger (aka the one with the baggage)
Ron Livingston had a good run on the series during its sixth season, making an appearance as Jack Berger, Carrie’s writer boyfriend, whom she meets through their mutual publisher at a book event. The two hit it off immediately, but the chemistry just about stops there for the remainder of their relationship. Not only did he never truly get over his ex, but he also has what is possibly the frailest male ego of the entire franchise. Berger holds grudges, can’t handle any criticism of his writing, lashes out when Carrie outshines him, and often gets defensive on behalf of all men whenever Carrie and her friends would dish over drinks. He also maintains a seemingly open channel of communication with his ex (who decorated his entire apartment) so the man is a consistently walking red flag through to the bitter post-it-note-break-up end.
6. Skipper Johnston (aka the "nice" guy)
Skipper Johnston (Ben Weber) is one of the first men we really see passed around and examined in the series, making his first appearance as early as the pilot when he rants to Carrie about nobody wanting to date the “nice guy.” She sets him up with Miranda, who quickly eats him up and spits him out, not finding his fumbling antics compatible with her own sharp personality. While she finds him cute, she never actively tricks Skipper into believing this is a relationship she wants to pursue. But Skipper quickly becomes obsessed—so obsessed that he breaks up with his new girlfriend while they’re still having sex only because Miranda calls him asking him to dinner. And it’s just that. So when Skipper blows up at Miranda for only calling him to have some fun, that’s an immediate no for me. Not only does he take out the frustration of his unspoken expectations on the woman he feels so strongly about, he brazenly discards another woman in the process. Not very nice of him at all.
5. Mr. Big (aka Mr. Commitment Issues)
Let’s face it: Big (Chris Noth) and Carrie are the heart of the series, the will-they-won’t-they to end all on-and-off TV relationships. While many vilify Big as being completely horrible towards Carrie (which he is, there is no denying this), he’s also extremely transparent with her the entire time that he’s not ready to commit to her. I can’t excuse his terrible behavior—from leaving Carrie at the altar to having an affair with her while they were both still in relationships—but the man rarely lied. At his best, Big is just a washed up bachelor finally letting loose within his seemingly perfect life, and Carrie is along for the ride. At his worst, he is an avoidant, non-committal narcissist who lacks the courage to actually act on or say how he really feels. Carrie just happens to be there waiting for him when he finally does.
4. Aidan Shaw (aka the one on his high horse)
Aidan Shaw (John Corbett) is often praised as the favorite of the bunch. After all, Carrie does cheat on him, and he still takes her back. However, go through their relationship with a fine-toothed comb, and you’ll see all sorts of red flags. The biggest offense may be that Aidan should have never dated Carrie in the first place, especially considering he has so many rules and deal-breakers for the relationship that he only discloses as they come up. He makes Carrie stop smoking cigarettes; he guilt trips her into staying in with him instead of going out; and he even makes her give up some of her favorite articles of clothing and shoes. The worst part is that all of these red flags fly under the radar that is the “nice guy” trope yet again. A man can be charming and down to earth but still be a toxic force.
3. Bill Kelley (aka the kink shamer)
John Slattery‘s charm only took this character so far in Season 5, offering fans a short-lived look at what it takes to be the girlfriend of a hot politician. He practically begs Carrie to date him after meeting in Long Island, and the two embark on their public and political agenda as a couple. The issue: He breaks up with her as soon as he realizes she doesn’t want to pee on him, a kink he reveals later on in their relationship. If the golden shower kink was enough to stop him in his tracks, Bill Kelley clearly never wanted a real relationship—and that’s a huge offense for the man who made a woman who doesn’t even vote attend so many of his political appearances.
2. Richard Wright (aka the one who hurt Samantha)
The biggest liar of them all, Richard Wright (James Remar) is the first man to really capture Samantha’s heart—and the first one to break it. When he’s caught shamelessly cheating on Samantha, he still has the gall to say he loves her. He might be the most malicious of the SATC boyfriends for not only lying about his feelings and expectations to one of the four leading ladies, but knowingly doing it. There might not be a single good bone in Richard’s body, and he absolutely relishes in that.
1. Trey MacDougal (aka the momma's boy)
Charlotte’s first husband, Trey MacDougal (Kyle MacLachlan), takes her through the wringer, costing Charlotte the most time, money, and emotional unrest for reasons mostly outside of her control. Trey only proposes to Charlotte due to the pressures of his overbearing mother, Bunny (Frances Sternhagen). Trey only reveals the night before their wedding that his sex life is touch and go. He even has practically no reaction when he learns that Charlotte kisses the gardener in a moment of weakness and discontent. He takes baths in the same room as his mother. He was never fully present during their relationship, and it is only after the papers are signed that he reveals his hand: He never wanted to play this game in the first place. And by this, we mean he seems more than happy to stay his mother’s little boy for as long as he lives. And for this, Trey receives the crown as the worst boyfriend ever.
