Yesterday Rebecca Feinglos, founder of Grieve Leave, shared with caregivers how to talk to their child or teen when ready to start dating again. As someone who went through this as a teen herself when her dad started dating, Rebecca shared the most empowering ways she believes parents can talk about about the subject. The next question: When is the right time to tell your child you’re dating, and how you can be reassuring? Read on…
When it comes to the right time for “the dating talk,” here’s what people might tell you: “Wait to introduce your kids to someone you’re dating until it’s really serious.”
My take? Not necessarily…
In my middle school and high school years, I remember meeting what felt like many women my dad dated. We talked about this a little bit toward the end of his life, that my dad wanted to make sure the women he went out with were kind to me and my brother. He didn’t want to hide the fact that his kids were the most important priority of his life. So, I think he made meeting us an early litmus test, maybe by the second or third date. Based on what I know now working in the grief space, I’d say that my father was probably more open to introducing us to his dates than the average widower. It didn’t necessarily bother me as a teenager, but I can imagine that dynamic might have been more difficult if I were younger.
Dad was always clear with us that anyone he was dating had to treat me and my brother kindly.
I don’t think your kid needs to know about every person you’re going out with. Far from it–especially for younger children who might feel connected with someone, only to have that relationship not work out. The whiplash of another perceived loss is especially difficult for a young child who’s already experienced the death of a parent. It’s another person taken away from them.
Here’s the key I’ve learned from both sides of this conversation: the introduction of someone you’re dating should feel like slowly turning up the volume, not blasting the music.
- Maybe it starts casually: “Sarah works in my office, and we’ve been working together for a few years.”
- Then evolves naturally: “Sarah and I have become close. We sometimes grab coffee or dinner after work.”
- Then opens a dialogue: “I’ve been enjoying spending time with Sarah. How would you feel about meeting her?”
This gives your kids something critical: agency. When you open up the introduction from jumping in the pool to dipping a toe in, you’re giving them time to process, space to voice their thoughts, and permission to have complicated feelings.
The timing of an introduction isn’t about a perfect moment–because there isn’t one. It’s about how you approach the conversation, how you create space for everyone’s feelings, and how you move forward together.
What people might tell you: “Reassure your kids that dating again doesn’t mean replacing or forgetting about their parent who died.”
My take? Yes, 100%.
Older kids need this reassurance, too–even if you think they already understand. Frankly, this is not a conversation I remember having with my father, and I wish I did. I think it was an assumption that my mother could never be replaced, that she was one-of-a-kind. But in retrospect, I wish I remembered hearing my father say that out loud in the early years of his dating after Mom died. In the back of my mind, I worried that Dad would just move on to a new chapter of his life as a single, dating, father–that the family photos that included mom would get taken down eventually (they never did, even when he got re-married.)
Dating is full of complicated feelings, all around–for you, and for your kids. I think the number one thing a widowed parent can do for their child while they’re dating is to keep an open dialogue about the grief that everyone is feeling. Assumptions are so easy to make, especially when kids are older. Don’t assume your kids know their parent can never be replaced: say it out loud. Don’t assume your kids know that you will always love their parent: say it out loud. Don’t assume your kids know you’ll never forget about their parent, just because you’re dating other people: say it out loud.
- For younger kids, that might sound like: “Sometimes grown-ups spend time with new friends to get to know them better. I still love and miss Mommy/Daddy, and I still love you, even when I spend time with new friends. That will always be true.”
- For tweens, that might sound like: “I might start having coffee or dinner with new people, on dates. I want you to know that no one could ever replace your Mom/Dad–I will always love and miss Mom/Dad. Your feelings about this matter to me–what do you think?”
- And for older teens, that might sound like: “Yes, I’m dating. Yes, it might feel weird for you–it feels weird for me too. I will always love and miss Mom/Dad–me dating people doesn’t change that. Your feelings about this matter to me–what do you think?”
Address these fears openly. Keep talking. Keep listening. And watch for signs that your kids might need extra support , like changes in behavior, school performance, or extreme reactions that don’t settle over time.
The bottom line: Remember: You choosing to date again is nothing to be ashamed of. You’re not betraying anyone by seeking connection. You’re not doing anything wrong by wanting companionship. You’re showing your kids that life keeps going after loss – not in a way that erases what was, but in a way that honors where you are now.
Take it slow. Stay honest. Keep those lines of communication open. Give everyone grace to figure this out together.
Because ultimately, this isn’t just about dating after loss; It’s about your whole family learning to write the next chapter of your story, together.
Rebecca Feinglos, MPP, Founder of Grieve Leave.
