13 of Charlotte York's boyfriends on 'Sex And The City,' ranked from trash to treasure

Michael forced Charlotte into a "blowjob tug of war" in season one, episode seven.

Episode: "The Monogamists" (season one, episode seven)

When Charlotte met Michael Conway (Jack Koenig) she told Samantha, Charlotte, and Miranda she might have found "the one." But that was before their "blow job tug of war" began. Shortly after they began dating, Charlotte learned that Michael considered not getting blowjobs a dealbreaker.  

Michael tried to lead Charlotte into a sexual act she was uncomfortable with on more than one occasion. 

He pulled her head towards his lap to initiate oral sex more than once as she tried to pull away. Charlotte remained calm as she eased away but was unsettled by the situation.

Charlotte explained to her friends that she hated giving oral sex and did not expect to receive it from her partners.

Michael gave Charlotte an ultimatum, and she opted to move on instead of backing down. 

Ranking: A soiled fried fish sandwich wrapper stuck to the bottom of a garbage can with no liner in a sixth-floor walkup apartment with no air conditioner on the last weekend of August.

Gareth Davis wouldn't wait until his date with Charlotte was over to start seeing someone else.

Episode: "The Cheating Curve" (season two, episode six)

Charlotte, an art dealer, brought Gareth (Sean Haberle) as her date to an opening she was throwing at the gallery where she worked — and then decided to make out with a random person during the party.

The seasoned gallerina was charming collectors and chatting with Carrie when the party ran out of champagne. Charlotte headed downstairs to retrieve more bubbly. She found her date dry-humping a twenty-something blonde up against a case of cheap demi-sec.

Ranking: The stench rising from Washington, DC, streets after an extended government shutdown. 

Alexander Lemley was an investment banker with intimacy issues.

Episode: "Are We Sluts?" (season three, episode six)

Charlotte met Alexander Lemley (Christopher Orr) at an art show. 

The wealthy New Yorker was handsome, sweet, and attentive to her needs — until they got to the bedroom. 

When he finished, he yelled, "you fucking bitch, you fucking whore," directly into Charlotte's face. 

Adding a few choice expletives to the bedroom can be fun, but only when it's consensual and affirming. Charlotte left their interactions feeling forlorn and devalued. She pointed out this habit to Alexander, and he decided to stop dating her and seek out a therapist to address the issue.

Ranking: Takeout you left too long in the back of the fridge that you did not realize was gross until you opened the lid.

Paul Ericson had a problem with public displays of affection — towards himself. He embarrassed Charlotte when they went out together.

Episode: "Take Me Out to the Ball Game" (season two, episode one)

It is hard to date someone you're horrified to bring out in public. 

Paul Ericson (Robert T. Bogue), the VP of a major recording label's classical and jazz division, could not stop cupping his testicles at events he was attending with Charlotte. 

Charlotte turned to Barneys to solve the problem when aggressively clasping Paul's hand failed. She purchased Paul a pair of high-end underwear with improved ventilation and extra support, hoping he would stop adjusting his genitals in public.

The plan backfired. Paul thought the gift was too intimate for a three-week-old relationship. "We haven't even made love yet, and you're out shopping for me? Slow down," he told her.

He dumped her for moving too fast. 

Ranking: The salmon burger leftovers you brought home from Sunday brunch and forgot to eat until Wednesday.

Ned, the merry widower, used his dead wife to pick up women.

Episode: "Four Women and a Funeral" (season two, episode five)

Charlotte stumbled into Ned, portrayed by Kurt Deutsch, at the grave plot of his departed wife, Liz. She was attending the funeral of a fashion designer named Javier when her hat flew off at the cemetery and landed on Liz's plot.

Ned and Charlotte made a plan to get drinks. He talked about his dead wife during their date. He even pulled out a picture of her to add seasoning to the sympathy stew he used to lure Charlotte in.

Despite warnings from Samantha, Charlotte fell for the sensitive widower act and began to believe she was just the woman to bring back Ned's libido.

Charlotte thought they were dating exclusively but learned that was not true when she arrived at a memorial service for Ned's wife. Ned used his sorrow to connect with several other women who came to the service.

Ranking: The trash bin in the playroom at your cousin with the three kids under four's house after a holiday break.

Jack was determined to have a threesome with Charlotte — whether Charlotte liked it or not.

Episode: "Three's a Crowd" (season one, episode eight)

Charlotte met an architect named Jack, played by Joseph Murphy, at a black-tie benefit for research into the Epstein-Barr virus. The two flirted throughout a series of other charity functions. When they began dating, he badgered her about having a threesome.

Jack used flattery to pressure Charlotte into kissing a woman at a party. He encouraged her to kiss the woman. Charlotte then wanted to explore a fantasy of having sex with Jack one-on-one in a bedroom at the party following the kiss.

In the midst of their escapade, the woman appeared in the bedroom, and Jack took the opportunity to fulfill his threesome fantasy. 

He completely ignored Charlotte, nearly knocked her off the bed, and left her feeling so uncomfortable she left.

Ranking: The gum stuck to the bottom of a brand-new pair of Manolos.

 

 

 

 

 

 

A magazine article attacking single women spooked Charlotte into dating a friend.

Episode:  "They Shoot Single People, Don't They?" (season two, episode four)

Tom (Tom Gilroy) was "an out-of-work actor friend" who had been in Charlotte's circle for years.  

Charlotte never considered dating Tom until a magazine article about single women scared her into thinking she would die alone.

They tried to make it work but were ultimately incompatible because they wanted things out of life. Tom cared enough about acting that he was willing to struggle and relocate to the West Coast for a chance to appear on a Christian soap opera.

Charlotte loved living the posh life in her Upper East Side neighborhood.

Ranking: A necklace you keep in your jewelry box and don't wear but never throw away.

 

Mike made a massive change to his anatomy that Charlotte appreciated.

Episode: "Old Dogs, New Dicks" (season two, episode nine)

Charlotte was uncomfortable with a guy she was dating named Mike being uncircumcised. She told him and her friends she had an issue with it.

Mike (Alex Draper) told Charlotte that being uncircumcised had caused issues for him his entire life, and he'd decided to get circumcised. 

When Mike healed from the surgery, he and Charlotte slept together. But afterward, he decided he no longer wanted to be in a monogamous relationship with Charlotte. 

He wanted to share a new version of himself with the world, and he was forthcoming about that.

He moved on, and she did not cry about it.

Ranking: A vacation trinket you lose when TSA makes you unpack your carry-on at the airport, but you're not super mad about it.

Brad, the bad kisser, brought Charlotte's dreams to a crashing halt with his cursed tongue.

Episode: "No Ifs, Ands or Butts" (season three, episode five)

"He raped my face," yelped Charlotte at breakfast with her girlfriends the day after a date with Brad (Ross Gibby), who she dated briefly. 

Chatlotte refused to give up on him even after an evening of lackluster lip-locking. She tried to work it out with Brad by teaching him to kiss softly and slowly. He would not take the advice.

Brad knew he was a lousy kisser, and it didn't bother him.

He was okay with leaving her chin sore. Charlotte confronted him about it in the middle of a kiss and then dropped him.

There were no hard feelings, just wagging tongues.

Ranking: A fun cocktail party story you pull out in awkward situations.  

Baird Johnson was a photographer with open ideas about gender. He was sexy and exciting.

Episode: "Boy, Girl, Boy, Girl…" (season three, episode four)

Baird was a photographer showing at Charlotte's gallery, played by Donovan Leitch Jr.

He challenged conventional ideas about gender in his work. Baird invited Charlotte to dress as a man so he could take her portrait.

He encouraged her to have fun by accessing her masculine side during the photoshoot.

The experience built Charlotte up and allowed her to explore what it was like to take charge in the bedroom. Their affair was short-lived, but it aided Charlotte's personal growth.

Ranking: The perfect clutch that tucks into your arm that you hadn't even planned to buy.

Stephen was a sexy pastry chef Charlotte had been friends with for years who finally made a move on Charlotte.

Episode: "Evolution" (season two, episode eleven)

Charlotte wore a casual look for an evening out with Stephen, a man she thought was gay.

Stephen, played by Dan Futterman, planted a surprise kiss on her before placing her in a cab at the night's end. She was shocked at his actions and the fact that she was wearing granny glasses when he kissed her.

Stephen confessed that he had harbored feelings for Charlotte for years, but Charlotte was reluctant to commit to him. She found his refined taste and impeccable manner too feminine for her. She enlisted her friends Carrie and Stanford to judge if he was "a straight, gay man or a gay, straight man."

Ultimately, Charlotte dumped Stephen for being afraid of a mouse. He squealed and jumped with her instead of rushing to protect her from the rodent. It turned her off. Charlotte ended up marrying someone with a controlling mother instead. It was her loss.

Ranking: The yummy soufflé you devoured on vacation. You wouldn't go out of your way to return for it, but you're still happy to have the memory.

Trey McDougal, Charlotte's first husband, was not a great husband, but he did shine brightly in the courting phase.

Episodes: Trey appeared in multiple episodes in seasons three and four.

Trey, portrayed by the amazing Kyle MacLachlan, may not have been able to stand up to his mother during his marriage to Charlotte. Still, he adored Charlotte while they were dating.

He showed Charlotte affection and respect. Trey understood that she wanted to take things slow and respected her boundaries.

He committed quickly and was ready to let her take the lead on little things like china patterns and home decor to make her happy.

Trey also supported Charlotte on more significant issues, like her decision to leave the workplace when they wanted to start a family.

Sadly, Trey was insensitive when they were facing intimacy and infertility issues. He also had trouble being honest about his feelings until he and Charlotte reached a boiling point. 

Trey prioritized his perspective over Charlotte's and had trouble choosing his wife's side over his mother's in arguments. His shortcomings did not erase his good qualities. He was just not the man for Charlotte.

Ranking: An heirloom you pass on to someone who will cherish it even more.

Harry Goldenblatt was the perfect match for Charlotte.

Episode: Evan Handler showed up as Harry Goldenblatt in season five of the original series. He stayed in the cast through the show's end and the 2021 reboot. He was also an essential character in the movies.

Harry was the most patient and loving man Charlotte dated. He was her divorce attorney when she and Trey finalized their split.

Like Trey, he let her dictate the tempo in the early stages of their relationship. She only wanted a sexual relationship, and he allowed her to have all the space she required. Slowly they began to spend more time together, and he grew on Charlotte.

When they began dating exclusively, he expressed his bottom line of needing his spouse to share his Jewish faith with clarity and conviction.

Harry's beliefs inspired Charlotte to rethink her Episcopalian roots. She did her research into his faith and converted.

They built a beautiful life together, more memorable than the fantasy Charlotte thought she wanted.

Ranking: Trey may have proposed with a Tiffany ring, but Harry was the 128.54-carat Tiffany diamond of Charlotte's love life.