Miranda Hobbes is a successful, and independent woman, who seemingly has everything, with a few great friends by her side. But one of the things that seems obvious in the show is Miranda’s interesting dating life. All four women have some ridiculous and questionable dating choices in Sex and the City, but it seems like the various men in Miranda’s life were particularly the worst, for one reason or another.
From the liars to the hotheads, these flings are enjoyable to watch on television but it would be interesting to meet these types of guys in real life. While she’s had some undesirables cross her path, Miranda’s also had some of the best boyfriends in the show. Overall, all four favorite fashionistas have had some of the most interesting dating moments in television history, and if they were all perfect, it wouldn’t be Sex and the City.
10 Tom: Season 5, Episode 4, “Cover Girl”
In the episode, “Cover Girl,” Miranda has given birth to Brady and in turn, is having trouble losing baby weight. She decides to join Weight Watchers where she randomly meets another member named Tom.
After meeting and going out for a date, Miranda and Tom find out they have more in common beyond having a Weight Watchers membership; they like to lean on each other to make bad food decisions. Tom wasn’t necessarily a bad guy, but he wasn’t a good influence on Miranda and vice versa.
9 Simon: Season 2, Episode 15, “Shortcomings”
At the gym, Miranda single father Simon Cobb and his son. After they all go for a walk, the boy whacks Miranda in the head, showing viewers where this is leading. Regardless, everything else seems good until one fateful morning.
After staying over at Simon’s, she’s relieving herself in the bathroom while naked, and Simon’s son tries to come in. She accidentally shoves the door back at him, causing him to hit his head. It was only a matter of minutes before Simon decides to choose his kid’s side, and sent Miranda packing.
8 Jack: Season 2, Episode 12, “La Douleur Exquise!”
In the classy episode named, “La Douleur Exquise,” Miranda meets a seemingly perfect man named Jack. Once they take things to the next level, Miranda quickly finds out Jack prefers to be intimate in every place but the bed, or other private places away from the crowd.
While this is fun and rebellious at first, Miranda just wants a normal-ish relationship, without the risk each time. When she sleeps over at Jack’s apartment, Miranda realizes mid-makeout session Jack’s parents are in town visiting. They walk into the bedroom, and Jack reacts like it’s the most normal thing to happen to him in the world… while he’s still on top of Miranda.
7 George: Season 3, Episode 10, “All or Nothing”
While Carrie was off proving to viewers that her relationship with Big was, for the most part, toxic, Miranda gets to know her colleague, George, who is in town for business. Coming from Chicago, Miranda’s fling with her cute Midwestern co-worker seems fun, but with the distance, there’s really not a lot of hope it’ll stick.
George and Miranda continue to talk on the phone after George leaves, and after several conversations on the phone, she finds out she’s not the only one George is talking dirty to. This duo was only together for a night or two so George isn’t technically the worst, but it is a weird situation to be in.
6 Thomas: Season 1, Episode 12, “Oh Come All Ye Faithful”
Up-and-coming playwright Thomas John Anderson seems perfect until Miranda realizes he immediately jumps out of bed to shower after they are intimate. At first, Miranda chops it up to good hygiene, but after a while, she learns it’s a result of his upbringing.
Nicknamed “Catholic Guy” by Carrie, Miranda finds out if this habit began when he was younger. The nuns at his church would repeatedly say being intimate was a sin, and Thomas couldn’t get past it in adulthood. Eventually, Thomas becomes defensive when questioned by Miranda, and their fling doesn’t last after that.
5 Detective Stevens: Season 3, Episode 17, “What Goes Around Comes Around”
Miranda’s hot and heavy fling with Detective Stevens began after Carrie is involved in one of the scariest scenes in Sex and the City history; she gets mugged. In fact, she got her shoes mugged right off her feet, and as a lawyer, Miranda is there for her immediately. This is when Stevens and Miranda click, and after a date out on the town, Miranda becomes self-conscious by how good-looking he is. One thing leads to another and Miranda has downed six martinis to ease the nerves.
After making a spectacle of herself after they went home together, Miranda wakes up alone, except for an AA number Stevens left her. Stevens was being kind because he’s used to helping people, but he should’ve been more accepting of the fact maybe Miranda was just nervous, instead of ghosting her.
4 Manhatten Guy: Season 2, Episode 3, “The Freak Show”
“The Freak Show” is an episode that would qualify Miranda as a good friend. While Carrie goes out with a man named Ben, Miranda decides to be a wing-woman of sorts and goes on a “non-date” double-date with Carrie and him. Ben brings his friend Luke, also known as the guy who hasn’t left Manhattan in ten years.
Luke shoots down any other city or state outside city limits, and after a short walk, Miranda has seen enough. After telling everyone she has to go “feed her cat,” Luke makes one last under-the-breath comment about cat people being “freaks,” which confirms Luke is sheltered and judgmental.
3 Harris: Season 3, Episode 12, “Don’t Ask, Don’t Tell”
By Season 3, Miranda has had her string of bad dates and decides to try speed dating out for a change. After telling multiple men that she’s a successful lawyer, she realizes that men don’t like powerful women. In desperation, she tells the next man she meets, a doctor named Harris, she’s a flight attendant.
Their chemistry is almost instant, and they start to sleep together. Everything changes one morning when Miranda is slicing a bagel and slices her hand opens in the process. She turns to Harris the supposed doctor and asks what to do. This is the moment when they both realize they aren’t who they say they are.
2 Kevin: Season 2, Episode 14, “The F*ck Buddy”
Miranda and Kevin are both lawyers and end up meeting in court after a screaming match. It’s clear Kevin is good at his job, but when it comes to dating, he’s bossy, overly-opinionated, and belittles Miranda. Miranda knows this isn’t healthy, but likes the intimate side of things. While Miranda is independent and strong, this short fling raises red flags, especially when she wipes off his beer glass in front of the girls. She can see situations that will set him off and wants to avoid them, which is alarming.
After Kevin is made partner at his firm, it’s evident that nothing will ever make him happy, and he’ll continue to belittle those around him. The positive side of this is that even though Miranda realizes she’s attracted to angry men, she wants to break that pattern right away.
1 Jim: Season 3, Episode 16, “Frenemies”
When Miranda’s date didn’t show up for a night out, Miranda finds out that he passed away. This leads Carrie and her to attend his wake and an “after-wake” party. It’s there that Carrie runs into a guy she used to go out with named Jim. Once in a band and now a civil engineer, it’s clear by the short conversation they had, Jim is still a little obsessed with Carrie, while Miranda thinks he’s cute. After Carrie warns her of how awful their breakup was, Miranda sees past it out of desperation.
It wasn’t until the three of them met up for drinks, and Jim’s old ways came to the surface. Jim can’t accept Carrie broke things off with him, even eight years later. Miranda finally realizes Carrie was right, even though it took her going out with him in the first place.
NEXT: Sex And The City: Carrie’s 10 Worst Flings, Ranked
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