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Falling in Love Again at Midlife

After the loss of her husband, this woman took a leap and found love

By Jill Smolowe

Widowed and divorced women who hear this story often tell me I was “lucky” — an odd thing to say, given the circumstance: At 54, after a happy 24-year marriage, I was widowed. Certain that I didn’t want to spend the rest of my life alone, I waded into the world of online dating in January 2010.

The “luck?” Seven months after Joe's death and 10 days into a rather dizzying tour of two dating sites that brought me into contact with a variety of men — some widowed, some divorced, all of them polite and not the least bit threatening — I heard from a guy who lived a few towns over. A water engineer named Bob, he had two grown kids and, like me, was recently widowed.

Taking the Leap

Though his picture was unappealingly stiff and his mention (twice) of wanting to find a “soul mate” made me wince (twice), several lines in his profile caught my attention.

In the “I’m looking for” section, he’d written: “A partner, a companion, someone with whom to share experiences, both good and bad, a best friend, a lover, an advocate, a defender.” I liked the dimensionality of that portrait, with its acknowledgment of both “good and bad.” Unlike the many guys who’d mindlessly reached for clichés about moonlit strolls along the beach, this man sounded thoughtful.

Bob also sounded like a realist. “Mutual respect and an ability to compromise are essential,” he wrote. My own profile had spoken of compromise and mutual trust, dynamics that had proved essential during my marriage to Joe.

Perhaps most appealing, just as I’d made clear in my profile that I loved my late husband, Bob wrote glowingly about his late wife of 38 years. Rather than feeling, as some women might, that I could never measure up to his deceased spouse, I considered his loving marriage a plus. To me, that suggested a man who knew what it took to create, nurture and sustain a partnership.

In subsequent days, we emailed back and forth, then switched to phone calls as our conversation deepened. A week after first making contact, Bob and I met for dinner at a restaurant. The next day, I removed my profile from the two dating sites.

Three years later, surrounded by his two children and my daughter, we married.

The Critical Elements

Bob likes to call our meeting bashert, Yiddish for “meant to be.” Me? I’m not a believer in fate. What I do believe is that each of us had a clear sense of our non-negotiables, which is to say the qualities we felt essential in a future mate.

Just as important, the timing was right. Though we were both still grieving, each of us had come to a place where we wanted to find someone with whom to share our lives.

To my mind, that timing element is critical. Had the so-called “perfect man” walked through the door sooner, I would not have been able to see or appreciate him. Two months earlier, I’d gone out one time each with two different men and, through no fault of theirs, realized that I wasn’t ready to welcome a new man into my life. I also hadn’t done my homework yet, which is to say I hadn’t figured out what exactly I was looking for. A dinner companion? A casual hook-up? A boyfriend?

My first hurdle was to acknowledge that I wanted a committed relationship and accept that moving forward with my life did not mean that I was leaving my love of Joe behind.

I still loved (and continue to love) Joe deeply. But as the months of grief accumulated, I’d become painfully aware that loving an absence was something quite different from loving a presence.

I wanted to love again. But I did not want to try to love again in the same way. I’d heard other widows say, with a hint of despair, “I’ll never find anyone like my husband.” Me, I didn’t want to find a replacement version of Joe. I knew that any man intended as his stand-in would never measure up to the original.


But, then, I wasn’t the original Jill. Experience, maturity, the jolt of loss and having to rethink who I was without the comfort and certainty of a partner beside me had given rise to a woman with priorities quite different from those that had guided the choice of my first husband. When I’d married Joe at 29, I’d been looking for someone with whom I could build a dual-career partnership, have children, set down roots in a community and raise a family.

Three decades later, with my nest about to empty and my career aims largely realized, I knew that the focus of any new relationship would be something else entirely. What I saw ahead was the winding down of my full-time career and an easing into a retirement that would be challenging to define. I wanted to be with someone who wanted a partner to chart and navigate that daunting terrain. Perhaps travel. Perhaps grandchildren. Perhaps volunteer work. Certainly a lot more “we” time than work demands and family life had afforded.

With Joe and me, the battles that we’d endured over the decades all had the same essential issue at heart: Whose time needs took precedence? That perhaps had been inevitable, given our two demanding careers. But I didn’t want to fight that battle again.

At the same time, I didn’t want that concern to impede me from moving forward. I knew many divorced men and women who had hesitated for years to forge new relationships for fear of “making the same mistake again.” That seemed odd to me.

To my mind, these friends were not the same people they’d been when they first married. They’d grown. Their understanding of relationships had deepened. Perhaps most important, their appreciation of what was missing in their first marriage had clarified. It seemed to me if they were genuine in their desire to forge a new relationship, that was what they would be looking for this time around, not what had made their previous marriage untenable.

Bob and I, who had both enjoyed long, happy marriages, could have been stopped by considerations more common to the widowed. Was moving forward with our lives a betrayal of the loved ones we had buried? Would new intimacy risk yet another loss? As it happened, we were very much on the same page.

We both believed that our desire to re-partner and to share our lives again was a testament to the strong unions we’d once had. Though we were still bereft, there was no confusion about whether Bob was seeking a stand-in for his late wife, Leslie, or I for Joe. From the start, we each knew that had we met earlier in our lives, it is unlikely we would have been attracted to one another.

Opening Up to Something New

Married now more than two years, Bob and I are proving well suited as we face the interesting, sometimes bumpy, challenges of figuring out what it means to craft lives around days that are no longer shaped by children’s schedules, in-laws’ expectations and job obligations. We stand as a couple distinct from our earlier, beloved marriages.

For those who, bruised by death or divorce, hover on the sidelines letting fear of potential injury trump their desire for new intimacy, I can offer this reassurance: For better or worse, it will never be the same.

This moment is different. The challenges that you face are different. You are different. If you can let go of the “Never again” mantra and open yourself to the possibility of something new, something different, something suited to the who you are now, the result can be astonishing.

Photograph of Jill Smolowe
Jill Smolowe is the author of "Four Funerals and a Wedding: Resilience in a Time of Grief." To learn more about her book and her grief and divorce coaching, visit Read More
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