Dating a Widower

Dating a widower can be challenging but rewarding.

I met him at 55 – handsome, smart, funny. Just the thought of him gave me butterflies. He was absolutely perfect. He was the man I’d been waiting for my entire life. And he was a widower.

He swore up and down that the grief from his wife’s sudden death five years earlier had long since passed. Then he swept me off my feet. That two people our age, so well-suited for each other, could find each other… It was a miracle. Then… BOUNCE! That fast. A Monday morning text. He’d fallen into a depression and couldn’t see me, talk on the phone, or even text. Poof! Gone. And just like that – heartbreak.

Did I miss something?

Did I do something wrong?

Is something wrong with me?

The answer, dear ladies, is a resounding no, no, and NO!

The Challenges of Dating

Older couple holding hands, relationships, dating a widower

Dating is fraught with challenges, even in the best of circumstances (aka young, upwardly-mobile, healthy, and child-free). Throw in age, aches and pains, money woes, children, elderly parents, divorce, and all the complications that come with aging, and you’ve got a recipe for disaster. Add a dead wife, and, well, you get my drift.

But with nature being nature, we all age. And with age comes a good chance that, at some point, we will date a man whose spouse has passed away. And with this comes confusion. Lives are more complicated, emotions are more complex, and mental health may be challenged. A widower could simply be out of practice dating-wise.

So, what’s a girl to do?

Be gentle. To him and to yourself. Know that complications can occur that have nothing to do with you but still affect you. Widowers can be “triggered,” wherein a hidden memory or feeling sends them into a spiral of irrational behavior. But if you can be patient and kind, and he’s willing to do the work, widowers are some of the best men because they already know how to love, communicate, and commit.

What to do when dating a widower:

Evaluate the situation.

Take your time to suss out where he is at emotionally and how you feel about it. Ask yourself, is he truly ready for a new relationship? There is no time limit for grief, and like the ocean’s waves, no two people grieve alike. Some are ready to rock after only a few months; others can take years. It’s not uncommon for a man to start a relationship with the best intentions, only to discover he’s just not ready. So, as with all relationships, proceed with caution and keep an eye out for red flags.

Accept the spouse that has died.

Even when a widower is looking for a relationship, that doesn’t mean the deceased spouse has been forgotten. One of the best gifts you can give a widower is an ear – to listen if and when he wants to talk about her. Allow him to tell his story. We girls tend to be pretty good at discussing our feelings with our girlfriends. Men? Not so much. They don’t have the same emotional resources and support we ladies have and might appreciate a safe space to share and feel.

Allow him to grieve on special occasions.

Man grieving while woman comforts him

Certain days of the year can hold more meaning and be more challenging for a widower – no matter how long his wife has been gone. Ask him how he would like you to support him at these difficult times. What can you do to make things easier? If he needs alone time, it doesn’t mean he doesn’t care about you. He has his reasons. Respect them, and…

Remember: It’s not a competition. 

It’s not about who wore it best or who he loves more. So, whatever you do, don’t get angry, cry, make demands, or complain. And for the love of God, don’t try to be like her. She will always be there. She will always be the one who came first… but the loss, however profound and painful it was for him, made him the man he is today. And that’s the man you want to be with.

Tread lightly when it comes to the kids.

You don’t want the children, young or old, to feel like you’re trying to replace their mother. As a rule, relationships should be on solid ground before introductions are made. And if he disagrees, take note.

Do NOT badmouth the late wife.

The biggest “don’t” of dating a widower is talking badly about his late wife. Period. Exclamation point.

Finally, and most importantly…

Pay attention to the red flags. 

Relationship red flags or warning signs to look out for

Because there are many. The following are some bright red ones. Don’t throw them in that box in your closet. Pay attention, and no matter how difficult, try to act accordingly – with reason and compassion – but not at the expense of your self-esteem. Here are the red flags you need to look out for:

He doesn’t acknowledge that you’re in a relationship. 

If you are consistently not invited or included in things that involve his family and friends; if he introduces you as a “friend” when you run into people in public; or even worse, he doesn’t want to be seen with you in public, then you’re a secret. This can make you feel like a mistress, which doesn’t feel good. Don’t put up with it. Not only is he sending the message that everyone else’s feelings are more important than yours, but this can ultimately erode your self-esteem.

He compares you to his late wife… 

Or he talks about her a lot. This could indicate that he’s not ready to move on – which means he’s probably still stuck in grief. Speak your truth. Tell him how you feel. If he can’t stop talking about his late wife, it’s probably time to leave. You know you deserve better.

You look like her. 

Does he mention ways in which the two of you are similar? Does he take you to places the two of them went together? Do you notice that conversations often start with “We used to …”? This could mean that even though you are dating, consciously or unconsciously, he’s stuck in the past. Remember, you aren’t his fallback plan, security blanket, or consolation prize. Instead, you are your own, unique and wonderful you, and should be treated as such.

He doesn’t know what he wants in a relationship.

Couple having a conversation about their relationship

If you ask him where your relationship is headed, and he can’t answer, it’s probably because he doesn’t know. And if you’ve been with him for a year and he still doesn’t know, odds are he’ll never know. The uncomfortable truth is that men, widowed or not, will commit to a relationship when they find the woman they want to commit to. And generally, as we mature, they know this sooner than later.

Now What? 

Don’t rationalize. 

“I’ll get used to it.” “He’ll change.” “It’s just going to take time.” Cut to: A year later, nothing’s changed. Sound familiar? When red flags and concerns arise, try calmly telling the widower what it feels like to be in your position. Talk openly but compassionately about how these issues affect you. Then note how he responds. Does he take your words to heart? Disregard them? Rationalize them away? Pay attention. Because in a healthy relationship, apart from being a good listener, you should be able to express your feelings and have them honored as well.

As always, you are your own advocate – your own number one. DON’T SETTLE. Expect the same behavior from a widower that you would from any man. And don’t let him treat you like anything less. If you are dating a widower, and want a long-term relationship, always remember: You deserve and should expect to be treated like the center of his universe. You deserve and should expect to be treated like the beautiful goddess you are.

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