Last year, I wrote about red flags to think through when getting ready to start dating again.  And though I stand by that post completely, I think my thoughts on this topic have evolved a bit.

Say you’re like me, mid-40s and divorced. The dating pool is therefore filled with other mid-40s and divorced people.  My bar, I joke with my girlfriends, is low:

Not crazy.
Didn’t kill his first wife.
No addictions.
Maybe kind of nice to me.
Maybe kind of attractive.
Loves Jesus.
Lives within an hour from my house.
Won’t beat me up.

Low, low bar.

And yet, there’s like 2.5 guys who meet that criteria.

I’m exaggerating, but still.  My bar seems low, but I think in the back of my head, I had other things on my list. Other, more restrictive, judgy things.

But I’m 43. And that means I’ve got 43 years of sin, 43 years of mistakes, 43 years of regrets, 43 years of baggage that I’ll be dragging into the next relationship.

And so, this man – this mid-life potential future man of mine – more than likely also has forty-something years of sin, of mistakes, of regrets, of baggage that he’ll be dragging into the next relationship too.

But I think a part of me was hoping for a non-difficult-ex, sin-free, baggage-free man.  There aren’t any, sweet ones.

Just like there aren’t any non-difficult-ex, sin-free, baggage-free us’ out there either.

So we might need to rethink things a bit.

Now, don’t get me wrong. I will raise the banner high for being wide-eyed, for being prayerful and discerning, for asking your friends to keep you on track.  If something feels off in your spirit, don’t ignore it.  If a hand is ever raised to you, run, don’t walk. If you are spoken to harshly  or controlled or manipulated or lied to during courtship, you’d better believe you will be spoken to harshly or controlled or manipulated or lied to during the marriage.

But if it’s his past, perhaps reconsider.

We all deserve a second chance.  We all deserve a fresh start.

When God looks at you, remember, he sees Christ and not your past and your sin and your regrets and your baggage. Thankfully. So, so thankfully.  And that’s what he sees when he looks at your next man as well.

So I want to encourage you to cautiously let grace abound. To perhaps consider that good man who treats you well with some skeletons in his closet.  You have skeletons too.  We all do.  It will be complicated…but at our age, everything is complicated.

But maybe, just maybe, you can just clean-slate your way together.  Carefully.  With God walking alongside.

And just think how gorgeous that redemption could look to the world.


Life isn't always how we want it. When change seems elusive, and we're stuck in old routines, a gentle push or some self-reflection can make a difference. Let these questions be that nudge to get you moving.

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