This is especially relevant for people dating in their 50s, 60s, and beyond. By that stage in life, most people have lived full lives. They’ve loved, they’ve lost, and they’re carrying experiences that shape how they show up in relationships.
Scott has written over 30 books and has a background as a psychotherapist, so he brings both personal experience and professional insight into this conversation. But what stood out most to me was how he reframed grief.
Grief Is Not Something to Fix
We tend to think of grief as something that needs to be solved. Something to “get over.”
Scott said something that really stuck with me: your grief is a testament to a life fully lived.
That completely shifts the perspective.
Grief isn’t a problem—it’s proof that you loved deeply. And if you’ve loved deeply, of course, there’s going to be pain. That’s part of the deal.
The issue is that a lot of people feel like they need to hide that part of themselves when they start dating again. They don’t want to seem “too heavy” or bring baggage into something new.
But that’s actually what creates disconnection.
You Don’t Have to Erase Your Past to Start Again
One of the biggest takeaways from this conversation is that moving forward in dating doesn’t mean forgetting your past.
You’re allowed to honor the relationship you had and open yourself up to something new.
In fact, when you’re honest about your experiences, you create the opportunity for a much deeper connection. You’re not pretending to be someone who hasn’t been through anything—you’re showing up as someone who has lived.
And that’s where real intimacy comes from.
The First Date After Loss Is Not Easy
Scott talked about what it felt like going on a first date after losing his spouse.
It was overwhelming. There was guilt. There was a feeling of betrayal.
And I think that’s something a lot of people don’t talk about enough. Even when you want to move forward, there can still be a part of you that feels like you’re doing something wrong.
That doesn’t mean you’re not ready. It just means you’re human.
There is no perfect timeline for when you should start dating again. It’s not about a certain number of months or years. It’s about when you feel emotionally open enough to let someone in.
Love Always Comes With Risk
This is something I talk about a lot in dating, but it hits differently in this context.
If you’ve experienced loss, you know firsthand that love comes with the risk of pain.
And because of that, it can feel safer to stay closed off. To protect yourself. To avoid going through that again.
But the alternative is also a choice.
You’re choosing a life without connection.
And most people don’t actually want that—they just don’t want to feel that level of pain again.
Commitment Matters More Than Chemistry
Another point Scott made that I completely agree with is the importance of commitment in relationships—especially later in life.
When you’re younger, it’s easy to prioritize chemistry and attraction. But long-term relationships aren’t built on that alone.
They’re built on commitment.
On choosing each other.
On being willing to work through challenges together instead of walking away when things get difficult.
That’s what creates stability. That’s what creates longevity.
What This Means for Your Dating Life
If you’re dating after loss—or even just after a difficult relationship—this is something to think about:
You don’t need to be fully “healed” to start dating again. You don’t need to have everything perfectly figured out.
But you do need to be honest with yourself about where you are emotionally.
And you need to be willing to let someone see you—not just the polished version of you, but the full picture.
Because the right person isn’t looking for someone who has never been through anything.
They’re looking for someone who knows how to love.
Final Thought
Love doesn’t end just because a relationship does.
It evolves.
And if you allow it to, it can show up again in a completely new way.
To find out more about Scott, check out his website here.
