Twenty years ago HBO unleashed Sex and the City to the world, changing the way women view modern dating as we know it. The series quickly became iconic due to its honest portrayal of sex and relationships from a female perspective. Being that the show is all about relationships, it’s no surprise that there were a handful of boyfriends the women have dated throughout the six seasons Darren Star has blessed us with.
Due to the show’s refreshing candor when it comes to dating in the modern world, a good portion of these boyfriends are not exactly people who you’d consider to be Prince Charming. On the other hand, there are a few love interests in the series that seem too good to be true. Below we have provided the complete list of Sex and The City boyfriends ranked from the absolute worst to the absolute best.
Jack Berger
No one on planet earth would start a fight over a freakin’ scrunchie unless you were as terrible as Berger. We can (barely) tolerate the fact that he needs to fall asleep to a Sharper Image sound machine that blasts frog croaking noises all night, but the fact that the sound machine was a gift from his ex? Come on, Berger…
If only picking up fights over retro hair accessories and falling asleep to obnoxious nature sounds were the worst of Berger’s problems. Unfortunately, the guy has a major fetish for women who are less successful than him, thus causing Berger to get super turned off when Carrie’s career skyrockets. Oh, and he dumped Carrie through a post-it note. He broke up with her using 7 measly words that said: I’m sorry. I can’t. Don’t hate me.
Well, Berger, we’re sorry, we can’t. We hate you.
Mr.Big
Carrie: I realized, to my horror, that not only did Big not love me, but he had no idea who I was.
Despite the fact that Carrie and Big end up together, we couldn’t help but wonder… was Big the literal worst? It’s one thing to be a commitment-phobe who is upfront about wanting to keep things casual, but to lead Carrie on and mess with her emotions for a whole decade? Granted, our girl Carrie B was all about the drama and subconsciously enjoyed the torture that was inflicted upon her by this 40-year-old baby, but that still doesn’t make any of his behavior acceptable.
Big represents all of Carrie’s worst decisions. This is especially highlighted during the plotline where she cheats on puppy-eyed Aidan with Big. There is a shot where the two are in bed smoking together, metaphorically revealing how Carrie’s most destructive addictions (Big and cigarettes) can only lead to trouble.
Trey Macdougal
Stale oatmeal has more flavor to it than Trey Macdougal will ever have. Despite Trey being Charlotte’s picture perfect man, their marriage is proof that everything is not what it seems. Trey refuses to communicate with Charlotte even when she is miserable in their relationship. He also has a major Madonna/Whore complex considering he cannot see his wife as a sexual being that has her own wants and needs after they get married.
Yet if it wasn’t for Charlotte’s marriage to Trey, she would have never met the love of her life! At least he had that going for him…
Richard Wright
Samantha gave Richard her heart, (both literally and in the form of a framed picture), and Richard couldn’t handle it. Anyone who breaks Samantha’s heart is a straight up monster of a human being, and Richard did it more than once. He cheated on Sam, lied to her about it, and wouldn’t hire her for a PR position because according to this lowlife women are “too emotional” to be successful in their careers.
Face it, Richy. Samantha will always be too good for you.
Aleksandar Petrovski
Aleksandar, aka “The Russian” was drawn to Carrie’s quirky and funny persona since the beginning. It’s nice that he appreciates Carrie for her personality, continuously referring to her as a “comic” (which might be giving CB a bit too much credit). “The Russian” seems like a total catch until the two move to Paris and he completely neglects his relationship with her. This leaves Carrie feeling isolated and depressed in a new city with a major language barrier.
Petrovski had so much promise, like when he danced with Carrie inside of a McDonalds. It wasn’t until later that we realized how when it comes to romance, he was pretty much all talk.
Skipper Johnston
Remember Skipper? He was the love-sick puppy dog who was head over heels in love with Miranda. Introduced in the pilot as a “website creator” and “hopeless romantic”, he was pretty much the Teddy Bear of the show who wanted nothing more than to make Miranda feel loved. The poor kid kept getting his heart stomped on by Miranda who never seemed to take him seriously. The character pretty much disappeared from the series around the second season, which is somewhat odd considering he was also Carrie’s good friend.
Maybe he was so heartbroken, he moved to another city!
Aidan Shaw
Carrie: The irony is, Aidan’s acting exactly the way I wish Big would have behaved and I’m behaving just like Big.
Aidan Shaw is the anti-Mr. Big. He is fully committed to Carrie, he is drama-free, and he actually seems to care about what goes on in her day-to-day life. Carrie can’t handle how easy-going their relationship is, bored to death over being in an adult relationship with Aidan. Despite the fact that he is a great boyfriend, Carrie and Aidan’s personalities clash too much for them to be considered the perfect couple.
While Aidan prefers spending the night in to watch TV and eat a bucket of fried chicken, Carrie lives and breathes for the nightlife in New York City. While Aidan is perfectly content and satisfied with a drama-free relationship, Carrie literally breaks out into a rash and has night terrors over how much the stability in their relationship is getting to her.
Steve Brady
Steve and Miranda are pretty much opposites. While Miranda is passionate about her career as a successful lawyer, Steve is passionate about Scooby Doo reruns. Despite his childish aura, Steve is able to love Miranda exactly for who she is regardless of the problems that arise because of their opposing personalities.
Steve sees their differences as a bonus rather than a bad thing and he is perfectly comfortable with Miranda wearing the pants in the family (while he lounges around in basketball shorts). Yes, he sometimes makes mistakes (like in the movie), but overall he is a quality dude who truly loves his woman and will work hard to please her.
Smith Jarrod
Smith is too good to be true. For one thing he is basically Ken Doll in the flesh, yet more importantly, he is a stand-up dude who works hard to win Samantha’s love. Smith chooses her over anyone else, regardless of the fact that he can have anyone in NYC. He sticks by Sam’s side when she develops cancer and he treats Samantha like a goddess while she (at the beginning at least) treated him like a piece of meat. Eventually, Samantha realizes how much of a catch he is, and she finally opens herself up to a relationship with him.
Smith Jarrod is pretty much a fantasy rather than an actual human. This is most notable when he is just a-ok with the fact that Samantha hooked up with Richard when she and Smith were pretty much still together. He even waits for her while the two are hooking up to “make sure she gets home safe”. Like, what? That’s not real human behavior, that’s just something straight out of a Wattpad story written by a fifteen-year-old girl. He is too pure for this world.
Harry Goldenblatt
Harry: Charlotte…Ever since the first moment I saw you, I can’t think about anything else! I’m f*cking Romeo over here.
And “Romeo” he is. Harry is the perfect man on Sex and the City and he is never afraid to tell Charlotte exactly how he feels about her. He worships the ground that Charlotte walks on and will drop everything to make her feel loved and appreciated. He has a heart of gold, a sense of humor, and is pretty much the dream man. His excessive amount of back hair is a non-issue when we get to see how wonderful of a boyfriend he is. And don’t act like you didn’t melt when he first confessed his desire for Charlotte.
So there you have it. Who do you think was the best and worst boyfriend on Sex and the City?
