Why the Third Marriage’s a Charm for 50-Year-Old Bride

A sketch of a woman in a wedding dress.

For her third wedding, author Leanne Delap chose to wear a creamy-white, ’70s-style jumpsuit with a floaty tulle cape that was custom-made by Pink Tartan designer Kimberley Newport-Mimran. Photo: Courtesy Leanne Delap

Something old, something new. After years of inner reflection and coming to terms with who she is now, a woman says yes to being in the moment and to Mr. Right.

I am standing at the front of a church in midtown Toronto, opposite the man I am about to marry. This is not my first rodeo, nor is it his. He is wearing a slim new suit in French blue, to match his eyes. Those eyes are misting up as he promises to keep me safe and warm; sentimental is the very first word anyone would use to describe him.

Not a chance was I going to wear white. And yet, I find myself in a creamy-white, ’70s-style jumpsuit with a floaty tulle cape looped over my shoulders, custom-made by Pink Tartan designer Kimberley Newport-Mimran. Inserting the outfits so high in the story may seem superficial, but stay with me please because ritualized clothing is how we process weddings. And I promise to show how this jumpsuit — and how I felt in it — is integral to the arc of our journey.

Our combined five children, ranging from late teens to late 20s, flank us at the altar. I should be scared at the exponential worry and responsibility we are both taking on. I am not, which is either a very good sign about the man standing beside me or it means I am delusional. We walked each other down the aisle, after the kids. And unlike at my previous weddings, as we walked in procession, time stood still such that I could take in the faces of all the people we love in the pews.

A photo of The author with her groom in the limo.
The author with her groom in the limo, June 2018. Photo: Martha Kehoe

Yes, I said weddings. On this gorgeous blue-sky Thursday afternoon in June 2018, I am 50 years old; my new groom is 59. And the burning question is: why the heck am I getting married for a third time?

I’m not alone in this late-to-the-altar thing. How inspiring was the wedding of Green Party leader Elizabeth May, 65, to John Kidder, 71, with a great big 500-person party this past April? And, as always, the celebrity set has been paving the way for later-life bliss: Ellen DeGeneres married for the first time at age 50. Barbra Streisand remarried at 56, as did George Clooney at 53, Katie Couric at 57, and Harrison Ford at 67. Marriage Hall of Famer Liz Taylor took her eighth trip down the aisle at 59. As for the need for toned-down mumsy bridal looks after a “certain age,” do we really think J. Lo, now 50, will make like a shrinking violet for her fourth wedding, to A. Rod?

The cliché of marriage scarcity over 40, especially for women, is stuck hard in the craw of the public imagination. It dates from a random report in 1986 in Newsweek, which stated that the odds were greater an unmarried 40-plus woman would be the victim of a terror attack.

True, many older couples live together, rather than marry: the Pew Research Center in Washington, D.C., cites a sharp rise since 2007 — 75 per cent! — in the number of people over 50 who are living together, for a mix of financial reasons (there can be tax and pension penalties for later-life marriage), paired with a new openness to cohabitation. But then, in the U.K., the Office for National Statistics revealed that (new) marriages are on the rise for the 65-plus set there: up 41 per cent for men and 56 per cent for women over the five years previous to 2014.

Statistics Canada does not break down comparable rates of new marriage by age group. But we can divine some overall trends from a 2018 Angus Reid poll that showed Canadians in general are saying “meh” to marriage, as about half of us (53 per cent) no longer find the institution relevant. This correlates with two major trends: the number of people living alone is rising, as are the number of people cohabitating at any age. The report concludes that this “could be a shift away from traditional values.”

So the question was why did my fiancé and I choose to get married? It took us a while, a love story that took shape slowly over nearly a decade of dating, with an astonishingly friendly break-up in the middle. The scenario was daunting. My husband-to-be, on our first date — a set-up — in the spring of 2010, told me he considered his life going forward as a tabula rasa, a clean slate. Now, that prediction proved a tad too hopeful, but it was a compelling pickup line. In my experience, most of the men you meet over 40 have, well, some suitcases full of shit. The image he painted was typical: optimism is the second quality people would cite about him.

A photo of the ride and guests outside the church.
The bride and guests outside the church. Photo: Shinan Govani

He had lost his wife to cancer four years earlier, and had only recently begun dating for the first time since university. He had put the time and hard work in on his own grief, focused tightly on his (then young) children, found comfort in his good group of close friends and his law career. But I believe everyone’s story is their own to tell, so I’m not here to categorize the depth and richness of his experiences before he met me.

Me, on the other hand, well, I was all baggage and weary from picking myself up and brushing myself off. And 10 drafts into writing this story, I can skip to the meat of what I concluded. My challenge was and is all about identity: how time and circumstance, growth and loss and experience change who we are. In love and life, timing is everything. As a dear and wise friend told me at the wedding reception, “He may not have been the guy you would have ended up with at 25 but he is very much the right-for-you guy now.”

If you are very lucky, you get to do all that growing within a supportive and flexible relationship. Otherwise, you find yourself, like me, and my husband, recalibrating who you are and what you want later in life. It is high-wire work and means you have to be willing to rethink the outdated identities and outmoded thinking you have been clinging to.

We are different and, oh, how I fight to appreciate that as a good thing. After all, compromise is the right thing to do, the only real path forward as a team, but it does indeed suck at times. Both of us were captains of our own ship for more than a decade, as unintentional single parents. We are both stubborn and proud and used to being in sole charge of a household. To wit: we were a bit stuck in our ways.

We like different things — he never met a sporting event he wasn’t passionate about; I’d rather spend my Saturday on a cooking project. He loves his mature tree-lined midtown neighbourhood, and we moved a mere three blocks from his old house; I find it buttoned-up and uni-dimensional and I actively miss the vibrant mashup of my former Queen West lifestyle. He camps, skis and golfs; I read — a lot. I think as I’m talking and revise and splash out insights in a “dynamic” manner. This is frustrating to him because he is careful (which, in turn, frustrates me) with the time he takes to consider and process.

I took some great free couples therapy advice away from a Zoomer interview I did a few years ago with Toronto psychologist Dr. Eliana Cohen. Here is what she said to me about later-in-life unions: “When new couples in middle age come to me, they already have exes and baggage, so that is another layer of problems.” But “middle-aged couples are more interesting. Therapy is more nuanced and complex.”

A marriage that starts in middle age can be very satisfying, she said. “When we are young, we are often looking for someone exactly like us. As we get older, opposites attract. We appreciate the differences more and how they enrich our relationships. It takes time to learn that we don’t see things the same way. When we are older, it is much more exciting to have a different opinion if you know how to work through conflict.”

Here is some more advice on mature love that I keep folded in my back pocket. Christine Meinecke, a psychologist from Iowa I also interviewed once, wrote the 2010 book Everybody Marries the Wrong Person. In it, she describes the secret to lasting love at any age is that: “We do not look to our partner to provide our happiness and we don’t blame them for our unhappiness. We take responsibility for the expectations that we carry, for our own negative emotional reactions, for our own insecurities and for our own dark moods.” Easier said than done, but I have been re-reading this line for 10 years now, hoping I will eventually internalize the wisdom.

When we were young, things used to be simple and clear cut: choose a subject you like, get a degree, graduate and you are practically on your way to a starter home, a dog and 2.5 offspring! You meet someone lovely and fresh and young and starry-eyed and, after a few years pass amicably, you move in together. Everybody else is getting married — why don’t we?

A photo from the author's first marriage in 1991.
First wedding, 1991. Photo: Courtesy Leanne Delap

Even before Instagram, weddings were a time in life that was hyper-documented. We remember weddings through pictures, and my 2018 jumpsuit will someday nestle in an album snug in its time and place in family history. And since I am using bridal fashion as a nifty literary device here, I will use the outfits I wore to take a look at how I’ve changed — and how my views on marriage have changed — over the seasons of my life.

The photos of my first wedding are starting to fade, and the fashion moments are certainly frozen in time! The year was 1991, and I was a shockingly naive 24-year-old. I had been working in my grown-up career, then as the assistant food editor at Toronto Life, for a few years. I had always been in a rush to get my life started, skipping grades and focused on a prize: I just didn’t know what that prize was. My first groom was, and is, one of the kindest, funniest and sweetest people I have ever met. I deeply regret hurting him. We were too young and had much personal evolution to do apart, or at least I sure did.

He and his groomsmen wore dove-grey morning suits; it was a luncheon wedding on a fall day of fluttering red and golden leaves. I wore something so ’90s — off-the-shoulder blush pink Dupioni silk, full-skirted, full-length. And since the ’90s are back in fashion with such a vengeance, I was not surprised when Princess Eugenie wore a very similar gown to her nuptials last year. Seems my aversion to bold white was already in play. In hindsight, I wonder if it was a fear of standing out? (Yeah, a bride is gonna blend!) Or perhaps it was traditional virginal associations?

My attendants wore bracelet-length navy silk princess-line dresses, to the knee, all very proper and ladylike for the formal church service and reception. But if the clothes were on the mark, the marriage itself didn’t last long. I once called it a “starter marriage” in print, a then-trendy term, but I would not call it that any longer. It was real, if short-lived, and I took more wisdom away from it with me than I probably deserved.

I also have nothing bad here to say about my second marriage, to the father of my children. It took place after said children were born, so technically my kids have been to two of my weddings. The year was 2002, and I was 34. Our kids were two and four. This wedding was also a Thursday evening, and it was a surprise for (nearly) everyone there. My assistant at the time — I was then editor-in-chief at Fashion magazine — sent out invites for a margarita party on the rooftop of a fancy French restaurant. We were married just before the guests arrived, with immediate family in attendance.

I wore a white bustier, but it was covered in graffiti that read “I heart-emoji John,” as in Galliano, with a full-length black satin skirt in Galliano’s signature bias-cut, with ruching at the waist and a slit to my thigh. This was not a church wedding. My groom wore sunglasses for much of the civil ceremony. It was a blast. There were a lot of margaritas served from frost-dewed silver jugs. I wore a sheer Hermès voile opera coat to the (very late) after-party.

A photo from the author's second wedding in 2002.
A photo from the author’s second wedding in 2002. Photo: Cheryle Smith

The demise of that marriage is as private now as it was public then; the exposed rancor is another great regret of my life. With time has come appreciation (for my part, which again is all I can know) for what was good and the good that came from it. I loved that man very, very much. And I have full respect for my former life partner as a co-parent today to our two truly wonderful children.

But little was I to know the next season of my life, the decade-plus as a single mother, was going to be hard as hell and a time in which I learned so damned much about myself. The excess suffering and financial hardship wasn’t necessary to earn those insights, but what matters for the purposes of this story is that I found an inner strength I am proud of, a buoyancy and a perseverance that I did not know I possessed. But the struggling also cost me and shoved my confidence off balance.

Which brings us to my reckoning and why I had so much trouble feeling ready to actually get married a third time. My identity had shifted once again, with the predictable but still poignant lurch of an empty nest: my kids left for university, and the rhythms of my life changed at the same time as my now husband and I were embarking on a new chapter. It is not an accident we chose (an instrumental version of) “Landslide” at the wedding ceremony.

A year onward and much therapy later, I think what I was afraid of was losing who I was again: the image I had of myself as the plucky single mom just didn’t mesh with the life we were embarking on together. If I had help and support and love and cherishing, was I still me? I know: we can be really, really stupid with our self-sabotage and negative thought patterns, and here I was about to blow the very much right thing for me, for us. It was a struggle to allow myself to believe that I deserved this good guy.

But back to late spring 2018, as the date sped forward into view, I dithered and dragged my feet about the wedding planning. I also defaulted to more harmful self-talk: I’m old, I’ve lost my looks and my mojo, I’m boring. Oh, and another dumb falsehood that I indulged myself in: that it was somehow unseemly, greedy and show-offy to fuss over a third wedding. All total crap, yes! But I wallowed in the quagmire of contradictions anyway.

So it was that I found myself with about three weeks to go. We had booked the church, organized our five kids onto planes, invited friends and family from near and far, chosen a menu and a fun location with a patio. Yet, I had nothing to wear.

Newport-Mimran, reigning Canadian queen of classy and appropriate dressing, took my somewhat panicked call and, to my great relief, took on the challenge, within my budget and in such a truncated time frame.

I went into the meeting waffling on about maybe a pantsuit, maybe in a bright colour. As before, I had already ruled out white, I think, because I was deathly afraid of looking like mutton in lamb’s clothing. Kim didn’t ignore me, per se. She just kept on sketching out a dreamy, louche ’70s-style V-neck, sleeveless jumpsuit with a sexy slit at the flared ankles. She cited Beyoncé’s equally stylish sister Solange Knowles’ white bridal jumpsuit as her chief inspiration and brought out a picture of Carolyn Bessette-Kennedy to show me how some soft tulle fabric could complement a garment with modern, clean lines. Genius move because, of course, I was sold on the glamorous associations.

She brought over some creamy white “scuba” material that she got very excited about. I agreed on how it would make for sleek lines on a jumpsuit and feel substantial and fitted. Then she started sketching that tulle shawl, to create drama at the shoulders and flow behind me but I could still feel was most definitely not a veil. Again, avoiding the virginal connotation was clearly a hang-up for me, and I have been a self-supporting woman for 30-plus years, so there was no symbolic “giving away” of me to my husband. That said, I fully support people of any age who want to wear veils or take someone’s name — you do you.

The fitting process very much clarified things for me, around how negative I was feeling about myself and how I was getting in my own way. I was forced to live up to my own lofty ideals: I’d been saying for years that women should rise above the noise and embrace aging. I’m still slender and I go to the gym every day, though I’m not the whippet-thin fashion editor I once was. And I avoid all cameras like the plague.

And you know what? On the day I went for the final jumpsuit fitting with Kim, I let the negative chatter in my head go. I had been talking about my daughter and my soon-to-be step-daughter and about how I wanted them to have a positive body image. And it hit me like a palm slap to the head: I was not walking that talk. Shut up, girl! Put on the darn white jumpsuit and get on it.

A photo from the author's third wedding in 2018.
Third wedding, 2018. Photo: David Cohen

On our wedding day, I woke up and did just that. I was present in the damned moment that day, for one of the few times in my life. My family is small but fiercely loyal, and that core group has somehow never made me feel like my life was a scandal even when it actually was. I am very proud of my friends, as in, I’m genuinely flattered they like me. They are a key measure of the success of my life.

My husband, who truly is a better, more conscientious, kinder person than I am in any measurable way, definitely got the wonderful family and friends he deserves. Everyone seemed really happy that day. Life is so damned tough sometimes, people told us it was nice to celebrate something happy.

Unlike the competitive Pinterest gymnastics that millennial weddings have become, our gen-Xer/boomer union was stripped down. No photo booth, no nitrogen ice cream station, no sundae or baked potato bars, no artisanal coffee or taco trucks, no Ball jars of fermented ramps wrapped in burlap, and no official hashtag or wedding font (yes, custom logos are actually a thing). There was just plain old-fashioned dancing and a simple vanilla buttercream slab cake with some flower-shop peonies plopped on top.

What we did have were speeches by all our kids. It makes me cry every time I think about them: they were heartfelt and funny and sentimental as heck. They all looked so grown up and poised! My son and daughter have been on our own little team for so long, so the fact that they were so gracious and they spoke with welcome and genuine happiness? Priceless.

Then my new husband’s older sons spoke, on behalf of their sister, and it was in those moments that I exhaled. I knew we would all be okay. The enormity of the loss that family endured — wife and mom, when those kids were just nine, 12 and 15 — had felt both overwhelming and unknowable to me for the many years I had known them all. But as the boys poured out their hearts that night, with their father’s naked honesty, they drew the threads together. And everything finally felt right.

All our kids “got” intuitively what I had been unable to let myself trust in. The dumb, trivial stuff — how I worried about looking fat and old in pictures, what kind of wine was served, whether the weather would hold up — none of it mattered.

So why did I get married a third time? Because he offered me peace, and I finally had the courage to say yes to that. And now I have the rest of my life to try to help him find peace in return. And we both got married again because hope lives on longer than either of us will.

A version of this article appeared in the November/December 2019 issue with the headline, “Third Time’s a Charm,” p. 94-100.