Cheryl holding a glass of rosé in a garden setting for her story about dating after divorce

Dating After Divorce: Ladybug Laughs

Dating after divorce came with new rules, new vocabulary, and one unforgettable orange bucket. Thankfully, I’d changed too.

Dating Has Changed Since I Was Last Here

The last time I dated, people actually called. On telephones. With cords. If someone liked you, they asked you out. If they didn’t…well, you eventually figured it out.

Fast-forward a couple of decades, and somebody suggested I try dating again. “Why not?” they said. “It’ll be fun,” they said. Clearly, these people had never downloaded a dating app.

Apparently dating now involves swiping, ghosting, love bombing, breadcrumbing, and enough unfamiliar vocabulary to make me wonder if I accidentally enrolled in a graduate-level sociology course. I honestly just wanted to meet a nice man. Preferably one with good breath.

As it turns out, that was asking a lot.

Dating After Divorce Apparently Comes With a New Dictionary

Nobody handed me the handbook. I would’ve appreciated one. Maybe something laminated. With tabs.

Because somewhere while I was busy raising children, working, doing laundry, attending school events, paying bills, and living an entire life, dating acquired its own language: ghosting, breadcrumbing, situationships, love bombing, soft launching. I was exhausted before I’d even met anybody.

Years ago, if someone stopped calling you, they stopped calling you. We didn’t name it. We just ate ice cream with a girlfriend and eventually moved on. Now apparently there are charts.

Still, I figured dating after divorce couldn’t be that complicated. I’d survived parenthood. Surely I could survive dinner.

That confidence lasted until approximately the bread basket.

The Date

He seemed perfectly pleasant. We met at a restaurant. He smiled. I smiled. Then he started talking. Unfortunately, so did his breath.

Now, before you judge me, we’ve all had an off day. Maybe he’d enjoyed onions for lunch. Maybe garlic bread had staged a hostile takeover. Who knows? I remained optimistic—until the waitress arrived.

The Romantic Flank Steak

She handed us our menus, and I barely had time to open mine before he looked across the table and said, “You know…we could probably split the flank steak.”

I blinked. Split the flank steak?

Now, I’m all for sharing dessert. Maybe an appetizer. But somehow, on a first date, splitting a steak felt less like romance and more like we were trying to stretch the grocery budget until payday.

Still, I smiled because I was determined to keep an open mind. Apparently my standards were feeling unusually generous that evening.

Then Things Took a Turn

At some point, he leaned in and began describing what he considered the perfect romantic evening. I was expecting something along the lines of a walk on the beach, watching the sunset, maybe a glass of wine on the porch.

Instead, he enthusiastically described lying in the back of his SUV under the stars. I wasn’t entirely convinced. Then he reassured me: “Don’t worry…I always keep an orange Home Depot bucket in the back for outhouse emergencies.”

I wish I were making this up.

I actually looked around the restaurant because I was certain someone had to be filming a hidden-camera show. There wasn’t. This was apparently a real date.

No…scratch that. It was just my life.

The Grand Finale

When the check arrived, I quietly reached for my purse. He smiled and waved me off. “I’ve got this one,” he said. Then he grinned. “You can get the next one.”

The next one? Bless his optimistic little heart.

I thanked him politely. We wished each other well, and I drove home wondering if perhaps my GPS and I should’ve had one more conversation before agreeing to this evening.

The Part About Dating After Divorce Nobody Warned Me About

Here’s what surprised me. The date itself wasn’t the important part. The important part happened on the drive home.

I wasn’t devastated. I wasn’t wondering what I’d done wrong. I wasn’t replaying every sentence trying to figure out whether I should’ve been prettier, funnier, quieter, thinner, more interesting, or more agreeable.

I was laughing. Really laughing. Because somewhere along the way, I’d changed.

Dating after divorce wasn’t about convincing someone to choose me. It taught me I got to choose too. And that felt very different.

Ah, dating. Sometimes you find chemistry. Sometimes you get a really good story.

Turns Out…

Dating has definitely changed since I was last here. But thankfully, so have I.

Years ago, I might have worried that a date like this meant something was wrong with me. Now? It simply gives me a great story to tell over chai tea. And honestly, that’s worth something too.

Maybe not every date needs to become a relationship. Maybe some dates simply become really excellent material. Frankly, the orange bucket has already earned its keep.

What Modern Dating Has Taught Me

If modern dating has taught me anything, it’s this: always carry breath mints. Know your own worth. And if anyone mentions an orange Home Depot bucket before dessert, go ahead and order the cheesecake.

You’re going to need it.

🐞 Stay Awhile…

If you’re not quite ready to leave the porch, here are a few more paths you might enjoy wandering down.

If you’re learning that a new chapter can be different from the one you planned and still turn out beautifully…
→ The Unexpected Joy of Starting Over

If you’ve spent years making room for everybody else and are finally learning to leave a little room for yourself…
→ My Calendar Is Full of Everyone but Me

And if your inner voice could use a reminder that you don’t need someone else’s approval to know your own worth…
→ Overcoming Negative Self-Talk: Finding Honey in the Hundred Acre Wood

🍃 Come Find Your Spot

If you’ve ever stepped into a new chapter and wondered who changed all the rules while you were busy living your life…

You’ll fit right in here.

Become a Cottage Friend, and I’ll send you my free Welcome to the Cottage letter series—five little notes filled with humor, hope, and gentle reminders that starting over can be awkward, funny, surprising…

and sometimes downright wonderful.

No swiping required.

No flank steak splitting necessary.

And absolutely no orange buckets on the porch.

🍃 Come Find Your Spot

The porch light will always be on. 🐞

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