Dating a Widower? Hear What Women Have To Say About It

dating a widower

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

I personally have never dated a widower, but I know a lot of men and women who have. From what they tell me, dating a widower isn’t easy. Then again, neither is dating someone who is divorced. What are the differences? What are the challenges of dating a widower? And, are there positives?


I decided to sit down with a group of women to talk about dating a widower. All have experience. Here are the highlights of the discussion:

1. How is dating a widower different than dating a divorced man?

In any other situation, finding a mate is all happiness, but with a widower, it can be tempered with guilt. Widowers feel guilty that they are still able to enjoy happiness, while the person they lost can’t. They might also feel worried about other people’s perceptions. In other words, maybe others will judge them for finding happiness again. They might think, ‘Does being happy make people think I didn’t love my spouse?’


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2. What are some challenges you have faced?

There are both physical and emotional challenges. Physical reminders–mementos, personal effects, wedding pictures are difficult to see around the house. And it’s hard to determine the right time to speak up. You don’t want to sound insensitive, but you want him to start letting go of the past and embracing the future.

That’s not easy to do if his late wife’s clothes are still hanging in her closet. Emotional challenges involve certain days of the year, like the day she died or her birthday. Also, holidays that should be joyful (like Christmas) sometimes serve as sad reminders to the guy, when all we want is to celebrate like everyone else does.


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3. What helps in having a successful relationship with a widower?

Communication is so important. You can’t assume you know what they are feeling. You have to have patience, but still be firm in letting him know what you want and need to be happy. It’s easy to fall into the trap of catering to their widow status rather than making sure your emotional needs are being met.

4. Any tips for someone dating a widower?


Don’t make demands, but make sure he knows what you need. Keep in mind that everyone has catered to him for a long time, and that could possibly cause him to be a little bit selfish. Not that it’s his fault, but he might forget how to date properly and might not make the effort.


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The widower needs to learn how to be sensitive to you, as you are to him. Also, don’t let insecurities build up about the past. Raise the issues as they come up.

5. Is dating a widower ever hurtful at times?

It is hurtful to wonder if he will ever love you as much as his late wife, if you’ll ever be the most important person to him, if his loved ones are comparing you. It’s hurtful to see that his identity is based on being her husband and you wonder if he can create a new identity. It’s hurtful to feel like you can’t experience a holiday without it triggering memories of her.

6. Anything you want to say to a widower who might be reading this?

 No reasonable person expects you to forget your spouse. Dating someone new is about finding balance. It’s about taking the 8 by 10 wedding photo in the foyer down, while knowing that your new girlfriend has no issue with you looking at photos of your wife whenever you want.


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We feel like if we say anything about taking the physical mementos out of site, you (the widower) automatically hears “shred everything” and that’s not what we’re saying. It just means put them in a more private place.

7. The bottom line?

It’s important to apply the same standards to a widower as you would to any other guy. The only difference is you might need to have more patience. Having standards doesn’t mean you aren’t empathetic to the pain he’s gone through. Don’t settle for less from him than you would for any other guy.

Like this article? Check out, “Dating Over 50: Are We In No-Man’s Land?”

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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

    100 Responses to “Dating a Widower? Hear What Women Have To Say About It”

    1. Alison

      My boyfriend is a widower. After being divorced for 15 years, it is the best relationship I’ve ever had. He is thoughtful, kind, fun. Even though he has teenagers, he makes time for me and makes our time together a priority.
      Yes, he talks about his wife often. I welcome it. He shows me the kind of love that I am sure he showed her. She was one lucky woman to be married to him. I’m one lucky woman to be his girlfriend.


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