Permission to Begin Again

Ten Dates. Ten Men. One Unexpected Love Story.

Dating after divorce is a lot like deciding to eat gas station sushi. You know it's probably a terrible idea, but every once in a while someone tells you they met the love of their life at Wawa, and suddenly you're willing to roll the dice.

This year one of my girlfriends looked me dead in the eye and said, "I think you need to go on ten dates." Ten.

Not because I was lonely. Not because I was desperate. Not even because she thought I'd meet my soulmate. Her point was much simpler. "You don't even know what you like. anymore." Ouch. She wasn't wrong.

Somewhere between marriage, divorce, raising twins, selling real estate, trying to keep everyone else alive and happy, and occasionally remembering to feed myself, I had completely forgotten what it felt like to simply get to know another human being.

So I agreed. Ten dates. No pressure to fall in love. No pressure to find "the one." Just ten opportunities to figure out what made me laugh, what made me cringe, where my boundaries had moved, and whether modern dating was really as terrifying as everyone claimed.

I treated it like a social experiment. The results were... unexpected. It was less The Bachelor and more National Geographic. Some of these men were fascinating. Some should have come with warning labels.

Names have been changed because some of these men still don't realize they were the lesson.

Droopy Dog

Droopy Dog met me at a local resort. He was kind. Polite. Well dressed.

Unfortunately, I spent most of the evening feeling less like I was on a date and more like I was conducting grief counseling.

Within ten minutes I knew intimate details about his wife's devastating stroke, his emotional struggles, his loneliness, and approximately fourteen things his therapist should probably have been hearing instead of me.

Sir...I ordered a Sauvignon Blanc. Not a psychology degree.

Then...He didn't open a single door. Now before you all start writing me angry emails...

Yes. I can open my own door. I can also pump my own gas, change a tire, and negotiate a multi-million-dollar farm sale. I still appreciate a gentleman. Call me old-fashioned.

Lesson #1

Don't ghost. I texted him the next day and simply said he seemed like a nice man, but I didn't think we were the right match. No disappearing act. No bread crumbing. Just honesty. Growth.

Brian

His real name wasn't Brian. But he reminded me of a Brian from college who followed me around campus with the enthusiasm of a Labrador retriever... and about the same conversational range.

Every joke I made landed with all the excitement of a wet sponge.

Sarcasm? Nothing.

Dry humor? Crickets.

Quick wit? Gone with the wind.

I think I actually watched the ice melt in my drink. After thirty minutes—which somehow felt like we had crossed the Oregon Trail together—I politely escaped to meet friends before my babysitter started charging overtime.

Lesson #2

Humor isn't just something I enjoy. It's who I am. I'm the funny girl. I tease.

I tell stories. I use sarcasm as a love language. I laugh at myself more than anyone else ever could. If I have to explain why something is funny...I'm probably explaining me.

And if you don't get my humor...you're probably never going to get my heart.

Popeye

Technically, we never met. But after approximately 7,432 text messages and enough cancelled plans to qualify for frequent flyer miles, I'm counting him.

His first warning? "You better look like your pictures." Excuse me? This from a man whose profile photos appeared to have been taken during the Obama administration.

Every cancellation came with an apology. A really good apology. Thoughtful. Detailed.

Heartfelt. Almost...too practiced. You know that feeling when someone's explanation sounds polished because they've delivered it before?

Like his ex-wife had already heard Version 12.0? Yeah. That.

Lesson #3

Words can be beautiful. Apologies can sound sincere. Promises can be convincing. But patterns tell the truth.

If someone consistently shows you they can't make time for you, believe that.

If they repeatedly cancel, believe that.

If their effort never matches their intentions, believe that.

Don't fall in love with someone's potential. Pay attention to their pattern. Because consistency isn't sexy. It's trustworthy.

The Priest

He wasn't actually a priest. Although he did find me...in church. Which, honestly, felt promising. Apparently, after the service he took it upon himself to figure out who I was and emailed to ask me out. I have to admit...I admired the confidence. It took six weeks for our schedules to line up, but eventually we met for dinner.

He was nearly twenty years older than I was. Orange enough to qualify as a traffic cone. And surprisingly charming. Confidence is attractive. So is being pursued. For a brief moment I thought, Well...maybe.

Then the accelerator hit the floor. Before I'd even decided whether I wanted a second date, he had mentally planned our future. He began inserting himself into my life in ways that hadn't been invited.

The biggest offense? Approaching my children in public as though he'd already earned a place in their world. Sir. These are my children. Not bonus content. Not until I say so.

And then...The letter arrived. Not a text. Not an email. A real, honest-to-goodness, USPS-delivered letter. Naturally, I forwarded it to my therapist...also known as ChatGPT. The analysis came back faster than a DNA test. Diagnosis? Run. Fast.

Buried among the declarations and assumptions about our relationship was one sentence I'll never forget.

"We should have just fucked."

Well. Thank you for making this decision significantly easier.

Lesson #4

Chemistry is exciting. Confidence is attractive. Being pursued can feel wonderful.

But none of those things matter if someone ignores your pace. Real intimacy doesn't rush. Real confidence doesn't assume. And anyone who pushes past your boundaries before they've earned your trust isn't offering love...They're asking for access.

The right person won't make you feel guilty for protecting your peace.

They'll make you feel safe enough to lower your guard when you're ready.

Chester

Chester lived just far enough away that neither of us wanted to risk two hours in the car only to discover we had the chemistry of a tax seminar.

His solution? A video date. Honestly...Brilliant.

We poured a drink, chatted for about forty-five minutes, and got to know each other from the comfort of our own couches. It was efficient, practical, and probably saved one of us a tank of gas and an awkward appetizer.

He was perfectly nice. But somewhere between discussing careers and favorite restaurants, I realized something. I wasn't crossing the Beltway for this man.

Now here's where I temporarily abandoned all the personal growth I'd been so proud of after Droopy Dog. Instead of sending the polite, mature, emotionally evolved text I'd practiced so well...I disappeared. Not forever. Just...enough.

Apparently Chester did not appreciate my newfound invisibility. A few days later the messages started.

"Well then..."

"I see how it is."

Nothing overtly rude. Just passive-aggressive enough to make me feel like I was being scolded by a substitute teacher. Oddly enough, instead of making me think, Maybe I should give him another chance...it confirmed exactly why I hadn't wanted a second date in the first place.

Lesson #5

One of the biggest lessons I learned was that chemistry isn't a checklist. He was nice.

He was employed. He could carry on a conversation. There wasn't a glaring red flag during our video date. There also wasn't a reason to drive another two hours.

For years I thought I needed a perfectly defensible reason to say no. I don't. "He's just not my person."is reason enough. And here's the funny thing...Before I ever had to explain my decision, his passive-aggressive texts confirmed the instinct I couldn't quite put into words.

Your intuition usually recognizes something long before your brain can articulate it.

Trust it.

Dorian Grey

Now we arrive at the plot twist. Dorian and I have never actually met. We've been chatting for months after matching on a dating site, but there has been one tiny complication...

He's married.

Before you clutch your pearls, let me clarify. He's in what he describes as an open marriage. Now, I don't pretend to fully understand the rules of that arrangement. Monopoly has fewer instructions. But he was completely transparent from our very first conversation, and I can respect honesty.

Ironically, the most unavailable man on this list has been one of the easiest to talk to. He's thoughtful. Intelligent. Gives good advice. Calls me on my nonsense. Encourages me when I need it. And somehow, despite meeting on a dating app, we've settled into. something that feels more like an unexpected friendship than a romance.

Will we ever meet? Probably not. And maybe that's part of the appeal. Because here's something I've had to admit about myself...Sometimes I believe that if a man just gets to know me long enough, he'll rearrange his entire life because I'm just that charming.

Ladies...That is not confidence. That's Disney. People are who they are. They have histories. Commitments. Families. Baggage. Dreams. Choices that existed long before we wandered into their lives wearing cute boots and good mascara.

Not every connection is meant to become a relationship. Some people simply arrive to teach you something, make you laugh, offer perspective, or remind you that meaningful connections come in many different forms.

Lesson #6

Stop trying to audition for the role of the exception. Sometimes the healthiest relationship is the one that never asks either person to become someone they're not.

No Way José

Some dates don't happen over dinner. Some happen over months. Some happen in your own imagination.

No Way José was someone I cared about deeply. For a long time, I held onto what he said.

"I'm just not ready for a relationship." Not with me. Not with anyone. Timing.

I believed him because I wanted to. The confusing part was that his words and his behavior were telling two completely different stories. He called. He leaned on me. He sought me out. We shared a level of closeness that never fit neatly into the little box labeled "just friends."

Looking back, I realize we had built something that felt like a relationship...without ever agreeing that it was one. That's a dangerous place to live. Because when there are no labels, there are no expectations. And when there are no expectations, one person is almost always writing a different story than the other.

Then life did what small towns always do. People talked. I heard he was asking friends to introduce him to women. Then I saw him with someone. Then I watched him kiss her intentionally in my view shed. It felt like someone had knocked the wind out of me. Not because I wanted him back. Because suddenly every conversation we'd had replayed itself in my head.

I wasn't asking, "Why her?"

I was asking, "Why did I believe something that never matched what I was seeing?"

That was the painful part. Not losing him. Losing the story I'd been telling myself. Here's what I've finally learned. People don't usually announce who they are. They just keep showing you. In who they call. In who they make time for. In who they pursue.

And sometimes...In who they don't.

Actions have always spoken. I was just listening to the wrong language.

Lesson #7

Never mistake emotional intimacy for emotional commitment. Undefined relationships often create undefined heartbreak. If you're carrying all the emotional weight of a relationship without the security of one, don't be afraid to ask what you're building.

Clarity may be uncomfortable. Confusion is far more painful.

And when someone's actions consistently tell a different story than their words...

Believe the actions. They are almost always telling the truth.

The One I Already Married

This one probably doesn't count. But it does. Because if this challenge taught me anything, it's that dating isn't always about meeting someone new. Sometimes it's about seeing someone you've known for years through a different lens.

Date number eight was with my ex-husband. Bean.

We've spent the last few years doing something I'm incredibly proud of. We've become really good co-parents. Somewhere along the way, we found our way back to being friends.

Not the polite, "We'll survive birthdays and soccer games," kind of friends. Real friends. The kind who can laugh together. Root for each other. Celebrate each other's wins. The kind who remembers why they fell in love in the first place.

One day he suggested we go out. Not because either of us was trying to rewrite history.

Just...to ask the question. "Is there anything still here?" The answer surprised me. Yes.

And no.

There is still love. There is still respect. There is still a deep appreciation for the life we built together and the two extraordinary children we brought into this world. He will always be family. I suspect I'll always love him. But love isn't always an invitation to go backward.

Sometimes it's permission to appreciate what was without needing to recreate it.

Very early in our relationship, I told him I was afraid to date him because I couldn't imagine losing him if it didn't work out. He meant too much to me. Funny how life circles back. That feeling never really left.

Today, I don't want to lose him again. Not because I want my husband back. Because I want my friend. Because our children deserve parents who genuinely enjoy one another. Who show up for each other. Who cheer each other on. Who prove that a family doesn't have to look traditional to still be full of love.

For us, the greatest gift wasn't finding our way back to marriage. It was finding our way back to friendship. I think that's where we're meant to stay.

Lesson #8

Not every love story ends in happily ever after. Some evolve into something just as beautiful. Love doesn't always disappear. Sometimes it simply changes its job.

Mr. Darcy

Sometimes life gives you exactly what you need. Just not for as long as you'd like. Mr. Darcy wasn't really a date. He was a ten-day summer romance.

We met through mutual friends while he was in town from across the pond for work.

There were no expectations. No swiping. No carefully curated dating profiles. No wondering if his pictures were from the Bush administration. Just two people who found each other at exactly the right moment.

From the very beginning, there was an ease about us. The kind of connection you don't have to manufacture. The conversation flowed. We laughed. We shared stories. We looked at each other a little longer than strangers usually do. It felt...easy.

When it was time for him to go home, neither of us wanted to say goodbye. I cried.

He admitted it was incredibly hard to leave. And for the first time in a very long time, I realized something that had absolutely nothing to do with him. My heart still worked.

After divorce...After disappointment...After wondering if maybe I had become too independent...too cautious...too guarded...I could still feel. Really feel.

We're still in touch. Whether our paths cross again isn't something I can control. Life has a funny way of bringing people together when the timing is right.

If that's our story...wonderful. If it isn't...I'm grateful for the chapter we were given.

Because not every beautiful story has to end with an engagement ring. Some stories exist simply to remind you that you're alive. That your heart was never broken. It was simply waiting for the right moment to wake up again. That butterflies don't disappear after fifty.

Lesson #9

Be completely present when something beautiful finds you. Not every person who enters your life is meant to stay. Some arrive simply to remind you of who you still are. And sometimes...that's the greatest gift of all.

Fed

And finally...There's Fed. This story is still being written.

Ironically, we met through a mutual friend. A few days later, that same friend asked if he could pass along my phone number. I said yes. Less than an hour later...Ding.

Ladies, I don't care how independent we become. I still enjoy being pursued. Not chased.

Not smothered. Pursued. There's a difference.

Fed has reminded me that dating doesn't have to feel complicated. It can simply feel...easy.

There aren't any mixed signals to decode. No wondering whether I should wait three hours before responding to a text. No analyzing punctuation with my girlfriends like we're trying to solve the Zodiac murders. Just...Good conversation. Shared laughter. Two people enjoying each other's company. What a wonderfully refreshing concept.

A year ago, I probably would have skipped ahead and started writing the ending before we'd even finished the first chapter. The old me was always searching for certainty. The new me has discovered something even better. Curiosity.

I don't need to know where this goes. I just need to know whether I enjoy where I am today. If this grows into something wonderful...Wonderful. If it doesn't...That doesn't make it a failure. It simply makes it a chapter. Because somewhere over the last ten dates, I stopped measuring success by whether someone chose me. I started measuring it by whether I liked the version of myself that showed up.

Turns out...She's funny. She's resilient. She's hopeful. And she's finally learned that she doesn't have to rush the story.

Lesson #10

Dating isn't a marriage proposal. It's simply two people sharing a moment to see if they'd like another one. Sometimes there will be a second date. Sometimes there won't. Either way... If you leave knowing yourself a little better than when you arrived...It was time well spent.

Date #11

Turns out...My girlfriend gave me the wrong assignment. She told me to find a man.

What she really gave me was permission to find myself.

Somewhere between awkward dinners, unexpected heartbreak, old love, new possibilities, and a few truly spectacular stories I'll never be able to tell in church...I stopped interviewing men for the role of "husband." And started paying attention to the woman showing up across the table.

She was funnier than I remembered. Braver than I gave her credit for. A little scarred. A little skeptical. A lot more resilient. She had survived divorce. She had built a business. She was raising two extraordinary children. She had learned how to stand on her own. But somewhere along the way, she'd quietly started believing that independence meant she didn't need anyone.

These ten dates reminded me of something I'd forgotten. I realized I didn't have to choose between being independent and being feminine. Turns out I could negotiate a multi-million-dollar farm sale...and still appreciate a man opening the car door.

I could build a life I was proud of...and still hope someone wanted to share it with me.

Those things don't compete with each other. They complete each other.

I also learned that rejection doesn't define you. Chemistry isn't compatibility. Closure doesn't always come with an explanation. Sometimes the best relationships simply change shape instead of disappearing. Sometimes the right people stay for a season. And sometimes...The greatest surprise wasn't finding someone else. It was liking the woman I had become.

So...Would I recommend the Ten Date Challenge? Absolutely. I laughed. I cried. I got ghosted. I accidentally ghosted. I met a narcissist. I met a gentleman. I fell a little in love. I fell a lot out of love. I rediscovered an old friend. I rediscovered myself. And somewhere along the way...I stopped wondering, "Why doesn't someone choose me?" and started asking, "Do I even want to choose them?"

That, my friends...was the whole point. Ten dates later, I still don't know how this story ends.

And for the first time in a very long time...I don't need to. I'm finally enjoying the page I'm on.

Now if you'll excuse me...I'm only about 90% certain Fed isn't secretly married, leading a cult, or using photos from 2008. Now that's a happily ever after I never saw coming.

Sincerely,

Me.

P.S. If you're wondering...Yes. I'd do all ten dates again. Although next time, I might ask for résumés, references, and proof the profile pictures were taken sometime this decade.