Starting With the Ending: The Unexpected Gift of Your First Date After Divorce

The first date after divorce is strange. Not because you don’t remember how to sit across from someone at a table. Not because you don’t know how to smile, make conversation, or ask someone about their life. It’s strange because it feels like stepping into a world you once left behind… only now, you’re not the same person who left it.

When I went on my first date after my marriage ended, I was nervous. It had been years since my very first date with my ex-husband. Back then, I was young, hopeful, and full of the kind of innocence that believes love is mostly about finding the right person and building a life that lasts forever. This time, I walked into the evening carrying something different, experience, grief, growth. And an awareness that endings are not hypothetical. They are real. Still, what surprised me most was this. I wasn’t nervous because I thought I would fail. I was nervous because I didn’t know what it meant to begin again.

Dating After Divorce Means Bringing the Whole Story

Before divorce, many of us date with an unspoken pressure - Could this be the one? Will this work out? Am I doing this right? What if I mess it up?

We carry expectations like fragile glass. We want the beginning to be perfect because we believe the beginning determines everything. But divorce teaches you something you can’t unlearn. Even a beautiful beginning does not guarantee a lasting ending. And strangely, that truth can make you calmer. Because you’ve already lived through what you once feared most.

“Start With the Ending”: A Song That Captures the Truth

There’s a song by David Wilcox called Start With the Ending, and the lyrics stopped me in my tracks the first time I heard them:

“The secret of a happy marriage
Maybe you should write this down
You wanna keep a love together
The best way is to end it now…”

At first, it sounds almost backwards and even harsh. But as the song unfolds, you realize he isn’t being cynical. He’s pointing to something deeply human. When pretending ends, truth becomes possible.

He sings:

“When there’s no pretending
Then the truth is safe to say
Start with the ending
Get it out of the way…”

That line feels especially powerful after divorce. Because divorce is, in many ways, the end of pretending. And dating afterward becomes an invitation to live differently.

Why the First Date After Divorce Feels So Different

On that first date, I didn’t know what to expect. But I approached it with a new sense of openness. Not the kind of openness that rushes into romance. The kind that says that I’ve survived an ending before, and if this ends too…I will survive that as well. Divorce removes the illusion that love is only successful if it lasts forever. It reminds you that relationships can be meaningful even if they are temporary. That realization takes away so much fear. There’s something oddly freeing about realizing that this doesn’t have to be forever to be real.

Dating After Divorce Without Illusion

Starting with the ending doesn’t mean you expect failure. It means you no longer cling to fantasy. It means you stop forcing the future onto the first conversation. It means you allow yourself to be present. Instead of asking, is this my next husband? You ask do I feel comfortable? Do I feel respected? Do I enjoy being here? Do I feel like myself? After divorce, you stop dating for the fairy tale. You start dating for the truth.

What Mediation Teaches Us About Love and Honesty

As a divorce mediator, I see this truth every day. Most couples don’t begin with hatred. They begin with love. But somewhere along the way, they stop telling the truth. Or they stop feeling safe enough to tell it. They start defending instead of listening. They start protecting instead of connecting. And eventually, expectations shatter, as Wilcox describes, “on the kitchen floor.” Then what’s left is something heartbreakingly simple. Just another human being suffering. Just another person trying. That’s why “starting with the ending” matters so much. When no one is pretending, the truth becomes safe. And truth is where real connection begins.

Happy Valentine’s Day. May you find the love of your life.