Skip to main content

A Widow Shares Her Journey in the Dating World

Dating in your late 40s with two school-age kids can be complicated

Kali Sakai

Published on: October 11, 2023

a widow on a dating app looks at her phone at night on a bed

Of all the possibilities in the universe, I never thought I’d be dating in my late 40s as a widowed parent of two school-age kids. Despite how daunting it can be at times, I discovered something that gave me hope and answered this key question: Now that I feel mostly ready, where do I start?

Enter the podcast “Dating After Death” and its semi-anonymous host (I’ll call her “Ms. Host”) — who is also a widow and mom. She’s protective of her identity because of her day job and to preserve the privacy of her family and boyfriend. In every episode, she reveals the most incredibly honest and insightful stories of widows and widowers who have bravely looked for (and in many cases found) love again after losing their forever person.

Many of them are also parents, and that is the aspect I want to focus on. Simply put, it can feel like you’re fumbling around in the dark when you’re starting out and trying to be sensitive to the feelings of your kids. I asked Ms. Host to share some observations and thoughts that might help expand on my limited experience dating as a widowed parent.

When I first set out on this journey, I got on the dating apps. Not only is that what everyone does these days, but, more importantly, it was a way for me to feel in control of the dating experience.

Ms. Host offers, “There are some apps that are specific to single parents, like Stir, but in general you will find other single parents on all of the dating apps. I would say most people are on Hinge, Bumble and Tinder, depending on their area or what they’re looking for as they date.”

It’s okay to go at your own pace

Even when a widowed parent feels ready, dating when you have a family that has experienced a significant life-altering trauma can get complicated. Personally, I was thinking about my needs as a companion-seeking, love-deserving adult on one hand. But on the other hand, I didn’t know what impact that process would have on my kids. All I really wanted from dating, at first, was a kind, agreeable adult male who would go to shows with me and discuss interesting and fun topics.

“I think that taking things slowly and being very thoughtful about those early interactions is why the kids and I have had a smooth transition in my dating,” Ms. Host shares.

When I first got on the dating apps, my eldest, who was 12 at the time, voiced concern about me replacing their father in our family; he assumed a new person would be coming in to tell the kids what to do. But that was definitely not what I was doing, nor would I choose someone who did not respect the existing family dynamic.

“The most important thing to convey to the kids is that their [deceased] parent will never be replaced by someone new,” says Ms. Host. “For me, I told my children that their Daddy taught me how to love. I told them that because of the wonderful marriage we had, I knew that I would want that kind of love again some day.”

Over the course of several months, an unconventional, long-distance match that simply started with friendly banter, online board-game sessions, exchanging music video links and talking for hours via FaceTime evolved into a deeply connected, bonafide relationship. I made sure to make space for the kids when it did, always keeping an eye on their comfort level. We scheduled regular times to talk and interact with him, doing activities together that my kids enjoy, such as playing video games, making holiday crafts and sharing their art.

“In general, I think it’s wise to wait to introduce anyone to your children as a love interest until you are certain they will be in your life for a while,” cautions Ms. Host. “I have heard from many widowed parents that their children attach to their new partners very quickly, so obviously we want to do everything we can to prevent another significant loss in their lives. Also, I know that I wanted to be able to fully trust the person I was bringing into my home, as I would never want to put my children in a position of not being or feeling safe.”

My boyfriend, the kids and I have been able to spend time together in person, too, which is probably unlike most situations since he lives two time zones away.

Cherish memories

All the while, we keep their father present in our lives through the stories we share and the photographs and mementos around the house that acknowledge he will never be forgotten. Whether a widow(er)’s new person is remote or local, Ms. Host says to make a point to talk about your late spouse.

“I think it is a sign to the kids that he [their dad] will always be a part of our lives, even when I have a new partner. My boyfriend also will ask my kids questions about their dad as a way to let them know that there is respect and care for his continuing place in our family,” she says.

Ultimately, there are bound to be challenging moments when inviting someone new into your life, and navigating the feelings and needs that come up for everyone involved. I think the best we can do is be honest and willing to listen to what the kids are going through, while staying true to our own hearts.

Ms. Host concludes, “If I could give one piece of advice to widows who are getting into the dating world, I would encourage them to try and let go of their guilt as much as possible. We didn’t choose this life, and we are just as deserving of love and companionship as anyone. It can be really exciting to date again and experience all the feelings, so try as much as you can to enjoy the process.”

Good luck to those who are putting themselves out there. If you are looking for some honest stories to inspire and reassure you about dating as a widow, listening to the “Dating After Death” podcast is a good place to start.

More perspectives on widowed parenting

Get the best of ParentMap delivered right to your inbox.

Share this resource with your friends!