I Dated A Widower And Thought It Would Be Easy. I Did Not Expect This.


I thought it’d be easy: no bitter divorce war stories; no ex-wife nitpicking at my kids and me. He’d be so grateful I sauntered into his life. I’d be so wonderful with his kids. He’d adore mine. Dating this sweet widower was a true second chance at love.


I’d beaten out all of the casserole ladies bearing their condolences. I broke through his grief and we laughed so hard, our faces hurt. After a long, arduous journey of single momming, I’d found the crown jewel. He was fifty-something. I was forty-something. I could finally begin my forever.

Then, the bubble burst.

Dating a widower was NOTHING like I imagined — and involved navigating new and difficult terrain.

I didn’t know what red flags to look for. I didn’t even know a widower had red flags.

Middle-aged dating is already a surreal experience without throwing in a widower’s issues. Reading online profiles and googling the identities of dating prospects is a part-time job. It can be exhausting just to find someone you’d enjoy meeting for coffee, let alone have a relationship with.

He stood out in the crowd because he was sweet and kind. He was easy to talk to and we clicked immediately. And he understood my full-time momming, as he was thrown into full-time parenting by default.

He was understanding, even supportive, when I had to reschedule due to kid issues. By the time we met in person, he felt like an old friend.

We clicked. We had chemistry. The first several dates were blissful. There were no contempt-filled conversations about an ex-spouse, no custody war stories, no anger over drawn-out court proceedings.

My life was filled with that chaos and it was refreshing to meet a guy with nothing but love in his heart.

So, what went wrong? The usual hurdles were nonexistent. The obstacles I encountered were totally foreign to me. We met only four months after her death. Perhaps it was too soon. But by whose standards?

By the time I was officially separated, I’d been emotionally divorced for months. I initiated my marital split, and was ready to restart my life by the time the legalities caught up with my emotions.

It wasn’t for me or anyone else to decide what defined “too soon” for him. Some widowers jump right into the dating pool, especially after caregiving a spouse with a long illness. Some need more time to process their new lives, but don’t know it.

He’d been though hell, and it showed in his eyes. He lost his wife to cancer and her treatment took her across the country to receive the best medical care available. She lived with her family of origin. He stayed behind with the kids.

He considered the distance to be his processing time. I trusted his judgment.

A month after we began dating, Christmas arrived. Since our relationship was new, I didn’t expect to spend the holiday with him. That would have been weird. But, I got my first insight into how difficult holidays were for him.

I understood that holidays with a widower would trigger wonderful memories, as they often did for me.

I didn’t realize how painful the loss would feel for him.

Dr. Elisabeth Kübler-Ross’ “Five Stages of Grief” was never meant to apply to the living. The psychiatrist’s research was about how those dying process their impending deaths. Her research indicated that terminally ill patients go through a series of five emotions: denial, anger, bargaining, depression, and acceptance.

The bereaved process grief in a nonlinear fashion: one day can be blissful and the next downtrodden. The days are punctuated with guilt.

A widower will often feel survivor’s guilt. He felt guilty when he was happy. He felt guilty about her death, wondering if he could have done something to save her. Then he felt guilty for being alive while she wasn’t. And he felt guilty for moving on with his life.

woman holding hands with a widower as they walk on a boardwalk
Photo credit: Adobe Photo Stock

It felt like for every step he took forward, he stumbled a little bit backward.

I looked like her and had similar personality traits. We even have the same name. It turns out, these are major red flags as the widower seeks to fill the void with replicas of his deceased spouse. I worried that he expected me to be her.

I tempered my concerns by rationalizing that of course he’d want to be with a woman similar to his beloved partner. His marriage ended unnaturally and he was still attracted to her “type.”

Probably, part of my rationalization was true. However, I ignored the nagging feeling that he was seeking a replacement wife.

Unlike divorce, where the relationship ended for a reason, death is an unnatural ending to a solid relationship. The question became, does his moving on with life and feeling happiness dishonor her memory?

I deeply respected her important dates, such as her birthday, but even that wasn’t enough. Our dating anniversaries felt bittersweet to him because of the anniversaries he didn’t get with her.

While I honored his everlasting emotional bonds, our relationship needed to be cherished and celebrated in order to thrive.

He had one foot in the past and one in the present; he couldn’t reconcile the two.

When a wife dies, she is idolized and her flaws are immediately forgotten. She’s memorialized both in real life and online. Her spirit is everywhere. I tried to feel like that was a beautiful thing.

But, I was constantly bombarded with her presence to the point there were three of us in the relationship.

I tried to fix the issues. I jumped in and helped with tangible things like cleaning his fridge and driving his children around. It felt good. I was part of the team. But her intangible spirit loomed over me.

I desperately tried to nurture him back to life to no avail. I silently prayed, “Pick me! Pick me! It’s okay to let her go.” But it wasn’t for me to decide when or if a man is ready to let their beloved spouse go.

Competing with a ghost is still competing with another woman.

In fact, it’s competing with idealized perfection and I’d never measure up. In the end, I realized I’m not a consolation prize and had to take a hard look at our relationship.

He didn’t have to stop grieving to find love with me. He just had to give himself to me on the earth side.

I learned a widower may be reluctant to tell friends and family about a new woman in his life. He may worry they’ll judge him for moving on too fast or won’t be open to the idea of seeing him with someone else.

He might also be concerned this new relationship will cause friction with family and friends who are still mourning. This concern especially applies to her family who may never be ready to see him with anyone besides their beloved deceased.

If he’s scrambling to make others feel comfortable with his new relationship and has no regard for you and the relationship you’re trying to cultivate with him, he’s still grieving.

If you’re introduced as a friend instead of a girlfriend, or worse, you’re not invited to events where he may run into someone he knew before his wife passed, it’s time for you to set boundaries.

You’re not his dirty little secret.

Neither of you is doing anything wrong, and he’s entitled to move on with his life.

Until he truly feels that way, he’s stuck with one foot in both worlds, leaving him unable to be fully present anywhere.

If a widower is dedicated to a relationship with you the photographs, ashes, shrines, and other commemorations will not be prominent. He’ll make his home comfortable for you. He will make physical space for new memories with you.

He’ll be able to both cherish the past life he had with her and look forward to wonderful adventures with you. He’ll be able to balance past love and present love. You’ll feel treasured.

You don’t want to be a replacement wife for a widower. You deserve to be loved in your own right.

Although I was his girlfriend and met his entire family, when her family was in town, I wasn’t welcome. It was awkward and hurtful. I tried hard to justify his behavior and he openly communicated his feelings.

He was wracked with guilt when confronted with the mere idea of me meeting her family. They were his children’s grandparents and aunts, so of course they came to visit. They wanted to be as close to the kids as possible.

He felt guilty about his in-laws’ loss. He felt like he wasn’t allowed to move on. Then he felt bad making me feel bad. He hoped I’d be out of town during the times they visited.

The whole thing was a mess I just didn’t need in my life.

Eventually, I was forced to realize he was still in deep sorrow and had a lot of healing to do before he was ready for a relationship. I was ready for a relationship and wanted to be with a man willing to walk forward in life as my partner. We parted as friends.

I learned a lot about love from the man who was unable to fully give himself to me. And for that I am eternally grateful.


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