Dating grief
Illustration by Ruth Basagoitia

The Other Side of Grief is a series about the life-changing power of loss. These powerful first-person stories explore the many reasons and ways we experience grief and navigate a new normal.

After 15 years of marriage I lost my wife, Leslie, to cancer. We were best friends before we’d started dating.

For nearly 20 years, I only loved one woman: my wife, the mother of my children.

I was — and still am — grieving the loss of a woman who’d been the Robin to my Batman (her words, not mine) for nearly two decades.

Still, quite apart from missing the woman I loved, I miss having a partner. I miss the intimacy of a relationship. Someone to talk to. Someone to hold.

The leader of a grief support group I attended talked about the “stages” of grief, but also suggested that it wasn’t as if you processed those stages linearly. One day maybe you raged, then the next you accepted your loss. But that didn’t necessarily mean you didn’t rage again the next day.

The group leader considered grief to be more of a spiral, winding ever closer to acceptance, but also taking trips through blame, negotiation, anger, and disbelief along the way.

I’m not sure I was ever onboard with the spiral analogy.

My grief seemed like waves radiating out from a droplet of water in a larger pool. Over time, the waves would be smaller and further apart, then a new droplet would fall and start the process all over again — a draining faucet trickling empty.

After some time, the droplets are less frequent, but I can never seem to quite fix the leak. It’s part of the plumbing now.

In many ways, you’re never “over” such an enormous loss. You just adapt to it.

And I suppose that’s where my daughters and I are now in our story of navigating our lives without Leslie.

Jim and Leslie Walter on an adventure at the beginning of their nearly 20-year relationship. Image by Jim Walter.

If you’re never truly over someone you love passing away, does that mean you can never date again? Never find another partner and confidante?

The idea that I had to make my peace with permanent loneliness because death had separated me from the woman I married was ridiculous, but figuring out when I was ready to date wasn’t easy.

When is it time to date?

When you lose someone, there’s a feeling of being under a microscope, your every move examined by friends, family, coworkers, and connections on social media.

Are you behaving appropriately? Are you mourning “correctly”? Are you being too somber on Facebook? Do you seem too happy?

Whether people are actually constantly judging or not, it feels like it to people who are mourning.

It’s easy to pay lip service to the sentiment, “I don’t care what people think.” It was harder to ignore that some of the people who might be confused, concerned, or hurt by my decision to date would be close family who’d also lost Leslie.

About a year after her death, I felt ready to start looking for another partner. Like grief, the timeframe for each individual’s readiness is variable. You might be ready two years later, or two months.

Two things determined my own readiness to date: I’d accepted the loss and was interested in sharing more than just a bed with a woman. I was interested in sharing my life, my love, and my family. The droplets of grief were falling less frequently. The waves of emotion that radiated out were more manageable.

I wanted to date, but I didn’t know if it was “appropriate.” It’s not that I wasn’t still grieving her death. But I recognized the very real possibility that my grief was part of me now, and that I’d never truly be without it again.

I wanted to be respectful to the other people in my wife’s life who’d also lost her. I didn’t want anyone to think that my dating reflected negatively on my love for my wife, or that I was “over it.”

But ultimately the decision came down to me. Whether others judged it appropriate or not, I felt I was ready to date.

I also believed I owed it to my potential dates to be as honest with myself as possible. They’d be taking their cues from my words and actions, opening up to me, and — if all went well — believing in a future with me that only existed if I was truly ready.

Why do I feel guilty? What can I do about it?

I felt guilty almost immediately.

For nearly 20 years, I hadn’t gone on a single romantic date with anyone other than my wife, and now I was seeing someone else. I was going on dates and having fun, and I felt conflicted by the idea that I should enjoy these new experiences, because they seemed purchased at the expense of Leslie’s life.

I planned elaborate dates to fun venues. I was going out to new restaurants, watching movies outside in the park at night, and attending charity events.

I started wondering why I’d never done the same things with Leslie. I regretted not pushing for those sorts of date nights. Too many times I left it to Leslie to plan.

It was so easy to get caught up in the idea that there would always be time for date nights later.

We never really considered the idea that our time was limited. We never made it a point to find a sitter so we could take time for us.

There was always tomorrow, or later, or after the kids were older.

And then it was too late. Later was now, and I’d become more of a caregiver than husband to her in the last months of her life.

The circumstances of her health’s decline left us with neither time nor the ability to paint the town red. But we were married for 15 years.

We got complacent. I got complacent.

I can’t change that. All I can do is recognize that it happened and learn from it.

Leslie left behind a better man than the one she married.

She changed me in so many positive ways, and I’m so grateful for that. And any feelings of guilt I have about not being the best husband I could have been to her have to be tempered with the idea that she just hadn’t finished fixing me yet.

I know Leslie’s life’s purpose wasn’t to leave me a better man. That was just a side effect of her caring, nurturing nature.

The longer I date, the less guilty I feel — the more natural it seems.

I acknowledge the guilt. I accept that I could have done things differently, and apply myself to the future.

The guilt wasn’t because I wasn’t ready, it was because by not dating, I hadn’t yet dealt with how it would make me feel. Whether I’d waited 2 years or 20, eventually I’d have felt guilty and have needed to process it.

Photographs and memories on display

Being ready to date and being ready to bring your date back to your house are two very different things.

While I was ready to put myself back out there, my house remained a shrine to Leslie. Every room is filled with our family and wedding pictures.

Her nightstand is still full of photographs and books, letters, makeup bags, and greeting cards that’ve remained undisturbed for three years.

The guilty feelings of dating are nothing compared to the guilt of trying to figure out what to do with a 20 by 20 wedding photograph over your bed.

I still wear my wedding ring. It’s on my right hand, but it feels like such a betrayal to take it off entirely. I can’t quite part with it.

I can’t throw those things away, and yet some of them no longer fit the narrative that I’m open to a long-term relationship with someone I care about.

Having children simplifies the problem of how to handle it. Leslie will never stop being their mother despite her passing. Though wedding pictures might get stored away, the family pictures are reminders of their mother and her love for them and need to stay up.

Just as I don’t shy away from talking to the kids about their mother, I also don’t apologize for discussing Leslie with dates (I mean, not on the first date, mind you). She was and is an important part of my life and the lives of my children.

Her memory will always be with us. So we talk about it.

Still, I probably should clean and organize that nightstand one of these days.

Not moving on, just moving forward

There are other things to think about — other milestones to address: Meeting the kids, meeting the parents, all of those potential wonderful terrifying moments of new relationships.

But it starts with moving forward. It’s the opposite of forgetting Leslie. Instead, it’s actively remembering her and deciding how best to move forward while still respecting that shared past.

This reboot of my “dating days” comes easier with the knowledge that Leslie herself wanted me to find someone after she was gone, and had told me so before the end. Those words brought me pain then, instead of the comfort I find in them now.

So I’ll allow myself to delight in the discovery of a great new person and try as hard as I can to keep the regrets and past mistakes I can’t control from spoiling that.

And if after all of that my dating now is judged “inappropriate,” well, I’ll just have to politely disagree.

Want to read more stories from people navigating a new normal as they encounter unexpected, life-changing, and sometimes taboo moments of grief? Check out the full series here.


Jim Walter is the author of , where he chronicles his adventures as a single dad of two daughters, one of whom has autism. You can follow him on .