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What to consider when dating a widower

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By Laura Stassi
Posted on May 07, 2026

Q: How do you woo a widower? And does it make a difference that I’m not a widow or if I knew his late wife?

—Tamara, Washington, D.C.

A: This is an interesting question, and it’s one many older women may be pondering, considering the lack of older available men. Coupled or not, women over 50 outnumber men in this age group.

Factor in the relationship status detail, however, and the ratio becomes even more lopsided. Almost half of all women 65 and older are single, according to the Pew Research Center, compared with 21% of men in this age group.

When an older man becomes newly available through widowhood, there may be a tendency to want to pounce, for lack of a better word. He was married, after all, so he must be “a good one,” and he’s no longer taken!

Women who were close to the dearly departed wife might be especially inclined to consider the widower a desirable partner. Remember that clumsy joke Martha Stewart made about waiting for her friends to die so she could date their husbands?

But as one widower told me, stumbling through dating made him realize that while he knew how to make his marriage work, that didn’t make him an expert on romantic relationships. Just because a widower clicked with one woman for a committed partnership doesn’t necessarily mean he’ll click with another.

Also, widowers may be less inclined than divorced men to recouple, according to a study from the Journals of Gerontology, which counted couples who were married as well as those who were cohabitating.

“I dated a widower when we were both in our 50s,” Amy told me via a social media post. “Though we had a strong connection, he was honest about wanting to date around” instead of being exclusive. “By the way,” Amy added, “his wife had been dead three years when we met.”

Regardless of what a widower’s future relationship plans might be, he needs time and space to process his loss before moving on. Tamara, I’d recommend treading lightly, with the aim of developing a friendship first, and then see where that eventually may lead.

One guest on my podcast told his story. Peter Lichtenberg, a geriatric neuropsychologist in Michigan, was widowed young, and 11 months after his loss, he started dating again.

“When you’re dating while you’re still grieving, you’re vulnerable,” he said. Eventually, he remarried but quickly came to regret it.

“I was in a fog, in a way,” Peter told me in a Dating While Gray episode. “I mean, I really expected for the relationship to be the same” as his first marriage, “and also, I was really wanting some normalcy to my life again.”

Peter’s second marriage ended in divorce. He subsequently tied the knot again — but sadly became a two-time widower when this wife died. Peter is now married, happily so, for a fourth time. He says among his wife’s many good qualities is her ability to respect his need to remember his two deceased wives in various ways, including establishing scholarships in their respective memories.

“When you’re widowed, that relationship continues, in a way, and you’re trying to find the place in your life that works for both” the past and current relationships, Peter said. “And that is very different from divorce,” he added, “where you’re clearly trying to let go for good.”

Peter would advise anyone dating a widower to share and embrace memories in ways that don’t interfere or get in the way of their own relationship.

So dating a widower may sound daunting, Tamara, but you may find that the effort is worth it. At least two readers think so:

“I’m dating a widower. He’s great!” wrote Linda in a social media post. “But I do wonder if I am a ‘rebound’ or if he’s processing grief. Who knows?” she added. “We are ALL a little goofy, or a lot goofy.”

“My partner is a widower with a 43-year marriage, and I am divorced after a 35-year marriage,” Elizabeth wrote. “The issue is not widowed versus divorced in my mind because we had both done the emotional work we needed to do to grieve our previous relationship, and we knew what we wanted and needed from a new one.”

“This has been a very easy relationship,” she added, “for both of us.”

Laura Stassi is host of the podcast Dating While Gray: The Grown-Up’s Guide to Love, Sex, and Relationships and author of Romance Redux: Finding Love in Your Later Years. Send your questions to Laura at newloveafter50@gmail.com.

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