Meet the Bride Who's Been Married, Widowed, Divorced, and Remarried

The two constants? Optimism and a sense of style

Updated 06/26/18

Photos courtesy of Bucky Keady

I’ve always been an eclectic dresser. I got my creativity from my mom. In the 1960s, when all the women in our small Massachusetts town were wearing twinsets, she rocked jumpsuits and kaleidoscopic Pucci prints. She once hosted a summer party in a white lace top and matching bell-bottoms. The outfit was completely transparent—the one conservative touch was the white bikini she wore underneath. After my braces came off in 10th grade, I got totally into fashion too. Thanks to a newly acquired Vogue habit, I understood that all it took to make a plain outfit a fabulous one was a Gucci belt or fantastic shoes or bangles stacked to my elbow. Style meant doing things a little bit differently. That’s why for each of my three weddings (a span of more than 38 years!), I chose a look that was perfect for who I was at the time, not one that was storybook perfect.

I met my first husband, Harry, when I was in college. He was my professor, married and 12 years older than me. We weren’t involved, but I adored him from afar. He was so smart and witty—plus, his brown eyes and bashful smile were hard to resist. A few years after I graduated, I got a job at my alma mater, and he and I reconnected. He was divorced by then, and we fell completely, ridiculously in love. I was 25 at our wedding. At six-foot-five, Harry was a full foot taller than me, so I was most focused on finding the right shoes. No heels could be high enough, but I splurged on a pair of Christian Dior sandals that I found at Saks—and I got the dress there too. It was a long-sleeved floor-length number in a translucent champagne fabric; taking a page from my mom’s playbook, I wore a slip underneath. I felt beautiful in that dress, but that was beside the point: I was just so excited to be marrying Harry.

On our honeymoon at my parents’ house on Nantucket, Harry became jaundiced, and we thought it was from eating too many oysters. But barely a month later, he was diagnosed with cancer. He stayed in the hospital most of the following year, undergoing surgery and chemo. When he made it through treatment and went back to teaching, we were overjoyed, and I simply refused to imagine losing him. I threw myself into my life—with Harry as well as at my job with a Wall Street bank that was as ’80s as they come. Who knew life could be so stimulating and satisfying? I even decided I was ready to have a baby, something I’d never thought I’d want to do. But when our adorable brown-eyed David was just an infant, Harry’s cancer returned. Again, he spent a year in and out of the hospital, with no happy ending this time: He passed away shortly after David turned one. And just like that, I was a 31-year-old widow. In addition to having lost the love of my life, I had a baby to take care of and massive chemo debt to pay off. I did my best—I’ve always been a coper. I doubled down on my career and tried to buck up and look my brightest (think Sigourney Weaver in Working Girl). I was still making sense of my new normal when a former colleague called to invite David and me to brunch. Chuck was intelligent, amusing, and sweet with my son. We dated less than two years before we got married. Everyone was so happy that I’d found somebody to take care of David and me. Looking back now, I realize my heart wasn’t totally into it. But I was so optimistic, and, it must be said, my dress was awesome.

By then, I was working at Condé Nast, running HR for a few magazines, including my personal bible, Vogue. Wendy, a market editor there, helped pick out my look: a dropped-waist Oscar de la Renta dress with a colorful beaded cummerbund. Divine! But pretty much the instant Chuck and I said “I do,” we went into counseling. I worried I couldn’t be what I thought he wanted. I’m not cut out to be a traditional yummy mummy! Still, I hoped we would figure out how to be happy despite our frequent arguing. The best thing we ever did was have our kids, first Max, then Hannah. When Hannah was five, I left Chuck.

A year after the divorce, I threw a cocktail party, and one of the guests was my former neighbor, Jim, who’d split from his wife a year earlier. We live in a small town, and rumors had been swirling that we were involved, so I jokingly apologized for the gossip. “It’s OK,” he replied. “What makes me mad is being accused of something that I’m not guilty of but sounds like so much fun.” I’d known Jim for ages and hadn’t thought of him that way... but he asked me out on a date, and then another, and the next thing I knew, I was in love. We make sense together, in our funny way. If I am a tightly wound toy poodle, Jim is a warm and steady Saint Bernard. I keep him amused, and he keeps me grounded. With perseverance (and humor), all seven of us—Jim, me, and our five kids—came to be a thoroughly modern tribe. Even so, I was twitchy about getting married again. I’d had such bad luck! Sixteen years into “casually dating,” Jim told me he’d had it and broke up with me for good. Nine months later, I was on the train to work when Adele’s “When We Were Young” came into my headphones. As I listened to the lyrics about seeing the love of your life for the final time, I started sobbing. I missed Jim horribly and couldn’t stop myself from texting him a link to the song, telling him, “I’m bawling my eyes out and thinking of you.” He wrote back, and we met for a drink, when he told me he was seeing someone new. I was devastated...and a little furious! How dare he be fine without me?

Well, maybe he wasn’t. He reached out a few weeks later to let me know that he was single. So I held my nose, jumped into the pool, and we moved in together. That was two years ago, and when we started talking about marriage, I was nothing but thrilled. Last summer, while vacationing in Paris (my fashion homeland!), he proposed. Our engagement lasted two months. Why wait? I’d wasted so much time already. On our wedding day, Jim was 71 and I was 64. I didn’t even bother shopping—I already had a fabulous gown, a bright-green beaded number with black organza piping from Kaufmanfranco that I got at Saks (I’m a loyal customer!) and amazing Louis Vuitton shoes. In the pictures, I look like I could burst with happiness. And I could have. It would be ridiculous to say everything is absolutely perfect. I’m type A and Jim is more...mellow in the housekeeping department. With five grown children and several sons- and daughters-in-law between us, we’ve given up on coordinating family Christmases. But Jim is my soul mate; when we’re together, I’m as relaxed as I’ll ever be. I am myself, 100 percent.

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