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Becoming Ms. Right after years of dating Mr. Wrongs

For decades I molded myself to stay in relationships that weren’t right for me. But I now have a new outlook on my future — and my worth.

I was 21 when I left my home in suburban New Jersey and moved to New York. I imagined my life in the city as the fairy tale sold to me by romantic movies — an endless parade of handsome princes who’d compete for my favor, pulling up beside me in long, black town cars to whisk me off to some pre-war palace. 

In reality, dating in New York proved to be much like renting an apartment. Over time, I found my standards sinking and replaced them with a senseless optimism that often bordered on delusional: a grimy, basement-level studio with no windows and a faint smell of sewer? I’d light candles! A man who never showed up on time, didn’t reply to texts and wouldn’t take me out in public? I’d try harder to win him over! 

After years of dating men who didn't value me, I've got a new approach to relationships — and life.
After years of dating men who didn't value me, I've got a new approach to relationships — and life.Courtesy Jillian Sanders

At 34, a man I’d been dating for almost a year tried to break up with me in front of the Apple Store on Fifth Avenue.

“I thought you loved me,” I told him, shimmying out of the way as strangers staring at their new iPhones whisked past us on the sidewalk.

“I really tried to,” he said. 

Some part of me knew this was the last word — he didn’t love me. But I took his rejection as a challenge. I begged him to give me another shot, a chance to prove my worth. For the next two years, I cooked and cleaned and impressed his friends and doggedly tried to convince us both that we could work. When we finally ended things mutually, I was resentful of the time I’d wasted and wished I’d had the courage to walk away outside the Apple store like he’d told me to do and my heart knew I should.

At 38, I left New York. I was tired of wearing heels, blowing out my hair and running through a revolving door of relationships in which I gave more than I got and accepted less than I wanted. 

I moved to Colorado, where the air was clean and people wore comfortable shoes. I started my own business. 

Not long after, I met Jim through a dating app.

Jim, whose name I’ve changed here to protect his privacy, was from the start the opposite of every slick culture vulture I’d dated in the city — men who initially turned my head with grand gestures and good grooming but who revealed themselves to be nothing more than that. Jim was ruggedly handsome, drove a Jeep and wore flannel. He had no social media presence and called me to plan dates. He exhibited old-fashioned manners that never should’ve gone out of style.

We both worked from home — he in real estate and I in PR — and in quick time, we settled into a cozy routine at his place, working, cooking, taking his dog for long morning walks. At night, we played hours-long Scrabble tournaments. We went on weekend camping trips and I met his friends. 

A few months into our relationship, I learned Jim owned multiple homes. I was surprised and impressed that his real estate ventures were going so well, and that he was so low-key about his success. His lifestyle was modest, his home filled with mismatched kitchenware, his idea of a romantic night a bowl of popcorn and a few episodes of “Seinfeld.” For the first time in my life, I felt I’d found someone with whom I could relax and be myself.

Over the holidays, we flew back east to meet each other’s families. In New Jersey, we slept on twin cots in my grandparents’ tiny home and ate Thanksgiving dinner around a small table with 15 of my relatives crammed next to each other. Jim was a hit, working on handyman projects around the house and charming everyone in his Brawny Man, gentlemanly way.

A few weeks later, Jim’s parents flew us to their vacation home in Florida for Christmas. Jim’s parents and siblings arrived on a private jet, and at the house, Jim and I were given a suite overlooking the ocean. His waterfront manor with an elevator and a heated pool was quite a stark contrast from how I’d grown up.

“How come you didn’t tell me your family has a mansion?” I asked Jim, and he seemed genuinely surprised.

“Is this a mansion?” he asked.

“If it has an elevator,” I informed him, “it’s a mansion.”

We spent most of that trip holed up in our private suite, me pointing out all the obvious rich things Jim’s family did and had. Jim seemed so independent from his family’s lifestyle, so completely removed from their wealth. He shopped at Trader Joe’s and flew coach! The fact I’d met someone who shared my values and was nonchalant about his family’s fortune made me certain of him. 

Me on my 40th birthday. I was so excited to start my life with Jim.
Me on my 40th birthday. I was so excited to start my life with Jim.Courtesy Jillian Sanders

Not long after Christmas, Jim suggested we move in together, that he buy a house for us to live in (it would be his fifth). His budget was unfathomable to me. Taking tours of houses with sunken bath tubs and swimming pools, I waited to feel the giddiness of my young dreams coming true. Here was my prince, sweeping me off to a better life! 

Instead, I felt anxious. When I moved across the country from New York, it was the first time I’d ever had a space of my own. I loved my small one-bedroom apartment and in order to move forward, I needed a commitment towards our future.

“I want to get married.” 

Saying the words surprised even me. Being a bride had never been high on my “to do’’ list, but I was 40 now, and I didn’t want to be a live-in girlfriend. If we were going to share a home, I wanted to be a wife.

"I’ll sign a prenup.” It was an offer I would have made to anyone, under any circumstances. Not romantic, but necessary, I knew. 

Weeks later we were at a jeweler looking at rings. I felt a little silly, but also excited. We agreed a ceremony at Town Hall with a small reception would be nice. 

Weeks after bringing up the idea of marriage, we were looking at rings.
Weeks after bringing up the idea of marriage, we were looking at rings.Courtesy Jillian Sanders

Shortly after, Jim made an offer on a house we both loved, but it fell through. We decided to put house hunting on a brief hold after the disappointment, but most nights we’d still search new listings side by side and I’d quietly pinch myself. 

I’d spent nearly 20 years climbing the ladder as a publicist for a series of high-level people and publications in New York, work that got me up early and kept me out late. I’d hard-knuckled my way through, chasing dreams and promotions into my late 30s. Now, scrolling through homes together, I marveled at how this man I loved could also be bringing such a charmed turn to my life.

We were finishing dinner one night and about to leave the restaurant when Jim cleared his throat. “By the way,” he said, “I met with my lawyer to discuss the prenup.” He averted his eyes from mine. “You know, even if you sign one, you’d still get a lot of money if we ever divorce. Apparently there are laws that entitle you to continue life in a way you’ve grown accustomed to.”

He said nothing else, so I responded, “What does that mean, Jim?” 

“It just made everything real,” he said. “No one ever plans on getting divorced.”

I reminded him that he just made an offer on a multi-million-dollar home. He chuckled. “Well, you can always sell a house.”  

I’d brought up the prenup initially, but this felt like a different talk, one not about money. 

“Let’s give it time and see what happens,” he said. “Maybe one day.”  

On the car ride home, I tried to process our brief exchange at the restaurant. I cried quietly in the passenger seat as Jim drove unfazed, listening to NPR. Two months earlier, we were looking at engagement rings. Now, I felt Jim didn’t want to marry at all.

Back at his house, we had a conversation where Jim made it clear that he didn’t want to break up, but didn’t want to marry, either. “Let’s keep things as they are,” he announced. That would be easiest for him. 

I stayed quiet, taking in what he was saying so casually. I nodded and listened. And somewhere in my mind, I flashed for a moment to the front of the Apple store, that moment of knowing it was over, and trying to will myself not to know. 

I saw, too, the emerging path of a sustaining fantasy — the dance I could do, the part I could play, trying and accommodating and whistling while I worked, dreaming that one day Jim would find me worthy of being his wife after all. 

The girl outside the Apple store would have abandoned my hard-won independence to make things work with Jim. I would have stayed, moved in, abandoned my wish to get married, given up my apartment and done what he declared was best for him. This time, though, I recognized the scar that each small sacrifice would make on my heart from living in a house I knew was worth more to him than I was. 

This time, I wouldn’t go down that path, because now I know I cannot convince someone to love me more or less than they already do. Being Jim’s girlfriend came with perks, but it did not come with his full commitment to me and our future. I didn’t want to waste my time on anything else. 

The next morning as Jim walked the dog, I packed up my things. When he came home, I said goodbye, drove away and did not look back. Jim did not try to stop me, and he did not get in touch again. 

I still believe in happy endings; they just don’t involve big houses, penthouses or black town cars sweeping me off into fairytale lives. Today, my happy ending is a small, one-bedroom apartment that I earned, and I am living the richest life I have ever known.