What I Have Learned From Dating Widowers
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Relationships

Sleeping With Other Women’s Husbands

What I learned from dating widowers.

photo concept of dining table cut in half with 2 chairs across from each other
Valero Doval

The first widower I dated introduced me to his wife. She was six feet under.

“Barbara, this is Jan,” he said, as we stood at her tombstone. “She’s come to take care of me now.”

I gulped. I had been dating this sweet man — I’ll call him Stan — for five months, long enough to know he sometimes cried himself to sleep. He had been married to Barbara for 40 years and been without her for seven.

Time does not heal all wounds, I know. For most of us, though, time numbs the raw agony. Not so for Stan. His desperate, codependent need for caretaking smothered me.

Lesson 1

If a widower’s emotional baggage is so heavy it requires a bellhop, gently send him packing.

My journey as “widower whisperer” began in 2018, when I joined eHarmony after a long relationship ended. I dated three 70-something widowers in 18 months, and I quickly learned that widowers and divorced men are different animals. For starters, divorced people have driven down life’s broken road, and many of us — I got divorced after 18 years of marriage — got therapy along the way. Widowers are often still “married” to their wives. They’ve suffered an unfathomable tragedy and, in my experience, have almost no clue how to live another day, let alone approach other women.          

“Divorce is a very significant loss, but it’s not the same as death,” said Sherry Schachter, a bereavement expert who has counseled thousands of widowers in 40 years as a clinician in New York and as a board member of the National Widowers Organization.          

She never asks widowers “How do you feel?” because she says so many men struggle with expressing emotion. Instead, she asks, “What did you do when your wife died?” Did they withdraw? Talk to friends? Seek a new partner? Did their adult children freak out, worried they’d fall prey to the first woman who offered them a casserole and a kiss?

What if the new woman takes Mom’s house, Dad’s attention and — God forbid — his money? Men are wired to “fix” things, and widowers often rush to “fill in the blank,” Schachter said. That was true of my Widower Number 2, Martin (not his real name), who came into my life six months after his wife died. He figured the best way to fix his pain was to replace his wife with another feisty blonde.

He was kind, generous and an easy conversationalist. Martin’s purpose in life, he said, was to provide for my “wants, needs and desires,” just as he had for his wife. He took me on trips, massaged my back and served me martinis while I luxuriated in bubble baths. For Martin’s 70th birthday, I got him goofy gifts embroidered with “70 & Sexy” — but, ultimately, sexy wasn’t enough. We had clashing opinions on every important issue.

Lesson 2

Not even chemistry and cocktails can bridge a vast political divide.

Enter Widower Number 3, a university professor who spilled out his theories about widowhood in such detail, I contacted him — not for a date, but for a story. Dan applied his research skills to his own grief. He read books and sought counseling for the first time in his life. After all, he was not the same man at 72 that he had been as a groom at 27.

Among the experts Dan contacted was Justin Yopp, a clinical psychologist and coauthor of the 2018 book The Group: Seven Widowed Fathers Reimagine Life. One father in Yopp’s group shared a common challenge. When he brought a date home and she saw photos of his late wife, in frames with “Mommy” spelled out in block letters, she told him she couldn’t be happy unless he took the photos down. He called her an Uber.           

Lesson 3

Loving with grace means embrace, don’t erase.

If you must compare yourself to the dear lost wife, address your insecurities before you date a widower. Dan got a real education when he started dating. One woman wanted money. Another had not had sex in 10 years and didn’t miss it. Another had dumped her last boyfriend because — you guessed it! — he refused to take down photos of his late wife.

Two years ago, Dan started dating me. We talk freely about how much he misses his wife — not only the beautiful Sue he had known, but also everything about her he did not know, every secret of her heart he did not ask. Like many long-married couples, they got into a comfortable groove and kept rolling, rarely discussing the deep stuff, the whys behind what they felt and did. If only he had known then what he learned from losing her: Grief is a privilege. It lives side by side with gratitude.

Each morning, as I watch the cardinals fly in the garden Sue planted, I whisper a prayer of thanks to the woman who loved my boyfriend, her husband, for two-thirds of his life. I think it’s tender when he leans over to kiss me and the wedding rings — his and hers — jingle on the chain around his neck.

Here’s the ultimate lesson

Our lives can have many loves and many chapters, and a new page doesn’t diminish what came before. On Dan’s bookshelves, pictures of me mingle with pictures of Sue. The shelves are sturdy enough. Our hearts are, too.

For more on how older women can enjoy satisfying sex lives, go here.

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