Charlotte York: All The Reasons Why She And Trey MacDougal Were Wrong For Each Other – And How Their Marriage Became The Best Thing That Ever Happened To Her

My previous post on Jessica Alba and comparing her marriage to Cash Warren to that of Miranda and Steve from ‘Sex And The City’ mentioned that the only one of the four core women in Carrie’s friend group that got her happily-ever-after was Charlotte York. She was the art consultant, hopeless romantic, whose main goal in life and means of fulfillment was to become a wife and a mother. She finally got her happy end with Trey MacDougal in season 3, episode 12, titled ‘Cheers to the end of my desperate-to-be-married single woman phase!’, which is totally something Charlotte York would say.

But of course, the marriage wasn’t meant to be, and Charlotte’s failed marriage led her to meeting the true love of her life – Harry Goldenblatt. Harry was her lawyer in her divorce from Trey, and she initially hired him because she found him unattractive, and therefore, thought there would be no romantic attraction to come out of it. The irony is uncanny, especially as this decision of hers was inspired as a means of not being be distracted by his more handsome colleague. The two eventually married and had two kids together. Charlotte even converted to Judaism for Harry. He didn’t force her to, and I think it’s important to mention that. She did it because SHE wanted to.

But I think it’s important to talk about and put more on an emphasis Charlotte’s doomed first marriage to Trey. Charlotte saw her union with Trey as her Fairytale Ending. But it ended up being her Fairytale Divorce, which led her to her Fairytale Ending – the real one – with Harry. There were many things wrong in the union between Charlotte and Trey. Many red flags were ignored by Charlotte l, mainly because she was mesmerized by her ‘dream man’. Charlotte and Trey were engaged before they had known each other for a month. Charlotte was dismayed to learn that Trey had a limp member and couldn’t get it up, but married him anyway. was hesitant to marry Trey, even right before she walked down the aisle, on their wedding day, but Carrie reassured her that his inability to have passionate sex was just a one-off due to jitters – a total lie, and Carrie knew it.

I personally think that anyone that was ever friends with Carrie would’ve been much better off had they not listened to any of her advice. She also told Miranda that Steve was a good guy and encouraged Miranda to keep coming back to him. We shouldn’t be surprised, though. This was someone that kept coming back to Mr. Big when she knew he wasn’t good for her. When she told Charlotte Trey had the jitters, she obviously didn’t want to hurt her feelings and make her even more devastated by not going through with the wedding when she was already in a wedding dress. In the long run, Charlotte ended up being more hurt by going through with the wedding.

The thing about Trey is that he really wasn’t a bad guy. He just wasn’t right for Charlotte. Their intimacy issues weren’t their only issues in the relationship. Though, it wasn’t even that difficult to see that it was the main issue in their relationship. That lack of sexual intimacy stemmed from Trey’s deep-seated issues with his overbearing mother, Bunny, who essentially saw Charlotte as a threat to their close bond, leading to Trey’s inability to fully connect with her physically and emotionally; essentially, he was unable to separate from his mother’s influence and see Charlotte as his own partner. Key factors as to why their marriage was so short lived were as follows:

• Oedipal complex: Trey’s strong attachment to his mother, Bunny, created an unhealthy dynamic where he struggled to be intimate with Charlotte, viewing her as an outsider trying to intrude on their mother-son relationship. 
• Sexual incompatibility: Charlotte desired a healthy sex life, but Trey’s emotional baggage and inability to fully commit to her sexually left her feeling unfulfilled. 
• Controlling mother figure: Bunny’s constant presence and disapproval of Charlotte further complicated their marriage, creating a sense of pressure and disharmony. 
• Rushed marriage: Charlotte’s desire to get married quickly might have also contributed to overlooking potential issues with Trey before committing. 

When I initially watched the show, I couldn’t relate to Charlotte whatsoever. I found her bland. To me, she seemed boring. Mostly, it was because of her princess-like persona in her endless desire to become a wife and a mother. As a young viewer, I found her to be tacky. I saw her as a woman who rushed through things and, in a way, forced things to happen to her. But Charlotte was also all about manifestation. She was lovestruck, impatient, honest, often closed-minded, and even completely cancel-worthy at times. But most of all, she was a dreamer. She’s also the ISFJ personality type. People who fit into this category are known to be extremely classy individuals who care about presenting themselves in the most valuable and cherished light. Just as much as I looked up to Carrie in my initial ‘Sex And The City’ watch with my mom and then questioned her character in my rewatch era once I grew older, I grew to actually adore and understand Charlotte as a character in my rewatch. And just to give you an idea of how much I loved Carrie as a character, Cosmopolitan was my favourite drink simply because it was Carrie’s favourite drink.

No matter the case, and despite all her flaws and mistreatment of others , Carrie did have good qualities about her. Carrie represented everything a woman was expected not to be by societal norms, especially during that era. She was in her 30’s, unmarried, had no desire to have children, smoked like a chimney, ate unhealthy practically everyday, and had unhealthy habits, such as buying too many shoes and outfits to go with them; ones that that she couldn’t actually afford. But at least she looked great. Single and fabulous? No, sing and fabulous! Charlotte was the polar opposite of Carrie, and contrary to my very outdated belief, that didn’t make her any less fabulous.

I was never as ‘desperate’ as Charlotte to find my ‘Prince Charming’. It was never a thought in my mind. I didn’t care to be in a long-term relationship, and I was very judgemental of the women who craved to be loved by a man. I was dating around, of course. But it was never my intention to get into a long-term relationship. I met my husband when we were in our early 20’s and have been together ever since. But even the fact that we’ve lasted as long as we have has been nothing but a complete surprise. I’m not even talking about motherhood. That wasn’t anything I ever wanted or dreamed of; not like Charlotte did. I knew I wanted to have a child with my husband; but only with him and by him. Maybe I’m just talking out of my a**. I was never looking for love in my 30’s like Charlotte and many other women do by that age. I never felt like I was on a timeline, or that my clock was ticking.

I was very judgemental of women like Charlotte. I didn’t understand that need for a partner when she herself was so successful already. In my eyes, she already had everything – a great job, a great family, a great group of friends, a great personality. Why not let things happen naturally instead of forcing it? When we first met Charlotte in 1998, that was all she could think about, as well as becoming a mother. She knew exactly what she wanted, and she worked very hard to get there. She was in her 30’s and her clock was ticking. She wholeheartedly believed in romance, and she believed she was worthy of experiencing it herself.

Charlotte spent the first two seasons searching for her perfect match. She was always the optimistic about life and is sensitive and nurturing in her friendships. But she could also be self-critical, which made her doubt her confidence at times. Even though she’d always been the conservative out of the group, but it didn’t stop her from showing her sexuality. But there was a drastic difference between her and Samantha, for instance. Santana had sex just for the sake of having sex. She didn’t ever care for companionship. It just suddenly happened to her with Smith, and she finally allowed herself to go when she was with him. Charlotte, on the other hand, had sex with the intention of finding her ‘one true love’. By season 3, she finally met her match, at least on paper, in Trey. He was the literal embodiment of her wishes: a wealthy cardiologist of the proper pedigree, social standing, religious affiliation, and romantic inclination.

The two have a total meet-cute; like the one you see in romantic comedies. Charlotte was mesmerized, and so was Trey. They have a whirlwind romance. Charlotte did everything right. She did everything by societal standards of what it meant to be a woman and a wife. She even stayed celibate before the wedding. She got the perfect ring. She had the perfect wedding. Her wedding dress was a Vera Wang design with a princess silhouette and lace flowers, and she had the wedding at Holy Trinity Church on the Upper East Side. Her man was everything and more. Her life, however, wasn’t anything she expected it to be. Her life with Trey wasn’t the fairytale story she envisioned for herself. She had the perfect everything, except for the perfect marriage. Again, it wasn’t that either Charlotte or Trey were bad people that was the reason why their marriage failed. Actually, the opposite. As a young viewer, I always wondered what the point was for Charlotte to get married to Trey. And then I realized that…

…Charlotte had to get married to Trey to realize for herself that there was no such thing as a perfect, fairytale life. It didn’t matter if she had the man of her dreams who looked the part. It didn’t matter if she did everything that was expected of her to prove her femininity. It didn’t matter if she had the perfect ring. It didn’t matter if she had the perfect wedding. What mattered was the life built with the other person – like the one she built with Harry. Her courtship to Harry was practically a disaster. Her wedding to Harry was a disaster. But she built a beautiful life with someone she least expected. She opened her mind to something new when she met Harry, and that was what made the difference.

Charlotte married Trey because she saw him as the perfect, traditional husband figure – a wealthy, well-established man from a good family, essentially ticking all the boxes on her checklist for a partner, and she was very eager to get married, rushing into the relationship without fully considering the underlying issues like his overbearing mother who would later become a major problem in their marriage; she essentially fell for the ‘image’ of Trey rather than the real person. Trey got married to Charlotte because she was the ‘ideal wife’. He was in his 40s. Getting married was something that was expected of him. Charlotte fit every checkmark for what a wife should be.

The main reason why their marriage failed was that they rushed into it. They became engaged before they had known each other for a month. They walked down the aisle before the seasons changed. It’s just not enough time to really get to know a person fully. But Charlotte was obsessed with the idea of marriage. She practically manipulated Trey into proposing at breakneck speed because of her desire to join the marriage club. She was so obsessed with her timeline that she completely forgot about what it took to make the actual marriage work. I don’t think she even thought about the marriage part. She just wanted to get married as fast as she could; not because she necessarily loved Trey, but because she wanted to have children.

Trey wasn’t perfect, and he had many issues to address, and those issues weren’t addressed with Charlotte; not before the marriage and most certainly not during his marriage, which was why the marriage crumbled. Trey was a well-respected medical professional who, when confronted with problems in the bedroom due to impotency, can’t even discuss them with his wife. It made him feel less of a man. Charlotte made it clear right from the beginning of their union that she wanted to start a family with him, and he brushed off her concerns because he was embarrassed about his inability to perform his ‘duties as a husband.’ He didn’t give Charlotte enough credit to try to work things out. He didn’t even trust himself enough to figure it out. If there is one thing that really got in between Charlotte and Trey’s relationship, it was his selfishness in making the marriage with Charlotte work because of his ego.

The one scene I keep coming back to when thinking of Charlotte and Trey is when he came home after work to see Charlotte and her friends having a ‘ladies night’. By that point, they’d been well into their infertility journey. Charlotte was told they only had a 15% chance of ever conceiving a child. Trey tried to make light of the situation and gifted Charlotte a cardboard baby – something she DIDN’T find funny. The vibe between Charlotte and Trey was…awkward, and it was hard to avoid. To lighten up the mood, Trey decided it’d be a good idea to tell Charlotte’s friends of the cardboard baby. He thought, as he said himself to Carrie, it’d be not HAHA funny, but silly. Charlotte became infuriated. He belittled her feelings, but his feelings were suddenly shifted when she asked how he’d feel if she gave him a cardboard penis. It wasn’t as funny to him anymore.

I didn’t fully understand the depth of Charlotte’s despair until I myself was going through infertility. It was heartbreaking to watch. To know that you’re going through such heartache and that the person that’s supposed to feel closest to you is mocking you instead of supporting you is daunting. Trey certainly lacked compassion and empathy for Charlotte’s feelings, but expected nothing less than perfection when it came to his needs. What I loved about that particular scene was seeing Charlotte’s 3 best friends. They were obviously taken aback by the carbon baby fight, but they made their stance very clear – they were always on Charlotte’s side. And Charlotte, showing elegance and grace even when she’s mad, swiftly said, ‘Without a baby, they’re all I have.’ She was talking about her 3 friends here. Though it was a sweet nod, it was actually sad. It gave an emphasis just how lonely she was in her marriage to Trey.

I couldn’t put the full blame on Trey, however. Charlotte was also being unkind to him. Trey eventually got over his issues with their fertility issues and even gave couples counseling a try. Charlotte’s obsession with having a baby took a toll on him. After repeated attempts to have a child through IVF, Trey understandably grew tired of using all his free time to try to conceive. Charlotte didn’t care. She, instead of even trying to understand where he was coming from, decided to put their names on an adoption list for a Mandarin child without consulting him. Trey had a lot of flaws about him, but when Charlotte began pressuring him and pushing harder and harder to have a child, without taking into consideration his insecurities and feelings on the issue, she became as much a part of the problem as he was. In that same scene with Charlotte and Trey fighting in front of her friends, she said he was denying her a baby because of his own selfish needs. That’s simply not the case. He didn’t want a baby. It was too exhausting for him to even think of a baby. He just wanted to concentrate on his Marriage to Charlotte, whereas she didn’t.

And I say this as someone who’d been in Charlotte’s shoes. Going through infertility is an agonizing experience, to say the least. Mind you, I was never this obsessed with having a child. I did IVF treatments, and after one failed embryo transfer, I told my husband I was okay with us living a child-free life. It was just a total miracle that I got pregnant naturally 3 months later. We, too, were told there’d be little to no chance we’d ever be able to conceive. With that being said, though I previously said Trey was selfish in the marriage, Charlotte was too. It was as though Charlotte never actually wanted Trey as a husband, but rather a sperm donor. Regardless of the fact that they were never on the same page in regard to having kids, going on about making decision that involves two people in a marriage is mind-boggling and never the solution to all problems.

This leads me to begin the discussion on Bunny, Trey’s mother; and boy, there’s SO much to be said. Trey seemed to be just a little too close to Bunny. He believed his mother knew best. He’d let her be the matriarch of the MacDougal clan, run his life in almost every single arena. From what clothes he wore, to what he ordered from a restaurant, to the sort of tschotskes he bought to decorate his apartment, he let his mother determine every action he ever took. In his Marriage to Charlotte, Trey always put his mother first, and that was a serious obstacle in a marriage. Charlotte was too headstrong for Bunny’s liking. She expected Charlotte to just accept that she’d be running his life, and now by association, hers, but to no avail. Trey never stood up for himself, nor for Charlotte. But Charlotte certainly always let Bunny know when she crossed boundaries. In hindsight, Charlotte didn’t marry Trey. She married Bunny.

I could relate to Charlotte’s frustrations with Bunny. I had the same exact frustrations with my husband’s father. He, too, was practically a third person in my marriage, and had the same exact qualities that Bunny showed. This factor almost destroyed the marriage. He made his feelings very well-known about me, and never shied away from hiding it. But there main difference a major difference between my husband and Trey, and that was how my husband handled the entire situation. My husband never treated his father the same as Trey treated his mother. He never even liked his father to begin with. If it wasn’t for us wanting a relationship with my sisters-in-law, he would’ve disowned him much earlier than he did. But things got so out of hand that even us wanting to have a relationship with my sisters-in-law wasn’t a good enough reason to keep him in our life. My husband had ti make a choice that would be best for himself and our family. Time and time again, my husband made it known that I, as well as our son, always come first. That’s exactly why I was never ready to end my marriage, no matter how hard it was to make it work. Charlotte’s marriage didn’t stand the test of time.

The most compelling scene of Bunny’s meddling in Charlotte’s marriage to Trey and practically being the third person in the marriage was when Charlotte attended a traditional Scottish ball with her newfound family. Charlotte had already planned to adopt a Mandarin child by that point and had already made arrangements to do so while also going through fertility treatments simultaneously. At the Ball, Bunny was being her usual self – snarky and sarcastic. She then had the audacity to tell Charlotte that she didn’t approve of her and Trey adopting a Mandarin child. When Charlotte told her it wasn’t any of her business, Bunny said it was, in fact her business. In her own words, ‘the MacDougal name will be carried on by son of your own; not daughters of the South Pacific.’ When Charlotte ran to Trey to validate her frustrations with his mother, he was more worried about his image than Charlotte’s hurt feelings. For Trey, Bunny’s word was always final above all else. If she said he wasn’t going to have a Mandarin baby, then he wouldn’t have a Mandarin baby. When Charlotte was just about to leave the prestigious event, Trey impeded her exit and yells at her to, ‘get a hold of herself.’ He coldly dismissed her concerns and tore a huge hole in her dress to make matters worse. Trey took his mother’s side, even though Bunny was clearly out of line and in the wrong. This very scene showed that he never really respected Charlotte to begin with.

Perhaps Trey showed the most respect, appreciation, and love for Charlotte in their separation and divorce than he ever did in their marriage. When Charlotte had plans for a photoshoot involving her and Trey to portray ‘the perfect couple’, Trey came home just as she was preparing for it. Things were bad between them by that point that they slept in separate bedrooms. They were anything but perfect, and the photoshoot was a mere lie to the public. As she was telling him to get his stuff out of the guest bedroom, he told her he wanted a divorce. The following day, as she was getting ready to do the shoot on her own, Trey still came to be part of it even though they’d just separated. When she told him he didn’t have to do it, he was adamant that it was the least he could do for her. By the time the photos came out, Trey had already moved out, but at least the public thought otherwise and had a completely different image of the very unhappy (former) couple.

Charlotte and Trey were gearing up for their divorce. Or better yet, Charlotte and Bunny were gearing up to divorce. Trey didn’t even have the decency to face Charlotte after his decision to separate and his mother do it for him. Trey had travelled all the way to Scotland in order to avoid facing Charlotte, and he didn’t even have the guts or the respect for Charlotte to meet her gaze from across the negotiating table. It showed that he was a coward who was never mature enough for a serious relationship – especially not with someone like Charlotte, who had no problem fighting her own battles and coming out ahead in the end. This doesn’t leave Charlotte as an innocent party, though. In the end, Charlotte did rush Trey into a marriage he wasn’t ready for. Nevertheless, Trey did finally stand up to his mother at the divorce hearing – from afar. He left a note which read, ‘Charlotte York was a wonderful wife. She did nothing wrong. Give her everything she wants. Seriously, mother. Stop.’

Charlotte ended up benefiting a lot more from the divorce than she ever did from the marriage itself. But not if you look at the bigger picture. What I admired most about Charlotte was her determination and her willingness to open her mind and be a learner. She was determined to get married and have children. When she got married to the man she thought was her ‘Prince Charming’ and realized it wasn’t for her, she opened her mind to other means. Had she not married Trey, she would’ve never even looked at someone like Harry as marriage material, simply because he didn’t have the looks and wasn’t attractive enough to be an ideal partner for her. She probably wouldn’t have accepted her child when they revealed to her that they were non-binary. It was her short-lived marriage to Trey that Charlotte wanted, but not the one she deserved. She deserved much more than that, and it was this marriage that led her to it.

If there’s anything I myself learned from Charlotte’s marriage to Trey, it’s to never force anything and always keep an open mind. Focusing solely on external appearances and societal expectations when choosing a partner can lead to a deeply unfulfilling relationship, highlighting the importance of compatibility, open communication, and an understanding that’s of the deeper emotional needs beyond the surface level; essentially, “perfect” on paper doesn’t always translate to a fulfilling partnership in real life. More so,

• Don’t settle for a partner based solely on image: Charlotte initially saw Trey as the ideal partner due to his wealth, status, and seemingly perfect demeanor, but this facade masked deeper issues like intimacy problems and a lack of emotional connection. 
• Open communication is crucial: Charlotte’s hesitation to discuss her concerns about Trey’s intimacy issues with him, and his own avoidance of addressing them, ultimately led to a failed marriage. 
• Self-awareness is important: Charlotte’s journey through this relationship helped her realize her own need for emotional fulfillment and to prioritize her own desires in future partnerships. 
• Beware of external pressures: The societal expectation of finding a “perfect” partner with a certain image can cloud judgment and lead to poor relationship choices.