Chapter 3: Too Much, Too Soon? My Dating Site Overshare Confession

Simon

Age: 47

Occupation: Video game developer

Hair: Receding, but deeply committed to the strands still holding the fort.

Looks: Cute enough.

His Hinge prompts had me laughing so hard I hit “like” before my brain had a chance to intervene. We messaged for about a week, then graduated to actual phone calls. Talking to Simon was like tuning into my own personal comedy show — sharp, witty, timing so good he could’ve charged admission.

Before we could meet, he had a business trip, and I was off to see the “best Elvis impersonator” with friends. (Don’t ask.) We agreed to video call once we were both back.

At the hotel, my girlfriends and I cried laughing reading his messages. They were practically invested in him: if this doesn’t work out romantically, at least keep him as a friend.

Back home, I nervously prepared for the video call. Relief: Simon looked exactly like his photos. (You know that’s rare enough to deserve fireworks.) The call went so well we set a real date.

Meeting in person was surreal. He was funny, sweet, and the kind of gentleman who still walks you to your car. At the end, he asked carefully if I wanted to see him again. “For sure!” I said, though Cupid’s arrow had definitely missed me. Still, I told myself maybe attraction is one of those “slow burn” things… (Spoiler: it was not.)

Date Two: snowshoeing in the woods. Yes, I willingly wandered into a forest with a near-stranger because he made me feel « that » comfortable. But Simon was open, vulnerable, even charming. He shared about past relationships, his mother, and how all of it shaped him. Hours passed like minutes.

Then came The Call. The morning before our next date, Simon phoned and started asking about my past — family, relationships, healing. Since he’d been so open, I figured this was a safe space. Wrong.

I shared honestly. His response? Panic. Judgmental comments. The classic “this is too heavy, I can’t handle this much baggage.”

Excuse me? The man who unpacked his entire suitcase of trauma in front of me suddenly couldn’t handle a carry-on?

I froze. He tried to soften it with: “Well, let’s still go on our date tomorrow and see.” (Oh, bless his heart.)

Shaken, I called Auntie Joan. She listened patiently as I delivered my tale. As I was speaking to her, I realized something important: my story belongs to me. The past versions of me are gone, but they built the woman I am today. No one has the right to weaponize that.

I decided to text Simon and end things. Opened WhatsApp, ready to type… and there it was. A breakup message from him. Saying almost word-for-word what I was going to say. How dare he? I wanted the honor of dumping him!

You’d think I’d feel relieved, but instead I spiraled. Chest pain. Tears. Overwhelming sadness. My brain screaming: Why are you crying over someone you weren’t even that into? Someone you literally just met!

Turns out, Simon wasn’t just Simon. He was the locksmith who accidentally opened a vault I didn’t know existed: fear of rejection.

And sweet Jesus, it was ugly in there.

That was the true beginning of my dating hiatus. Not because of Simon the man, but Simon the mirror. He showed me where I still had work to do.

Every failed dating experience isn’t a verdict on our worth. It’s more like a compass pointing us inward, showing us what’s really happening beneath the surface. Simon wasn’t “the one” — he was the mirror. And mirrors, while sometimes unflattering, are still useful.

If anything, he reminded me of a hard truth: we don’t attract what we want; we attract who we are. Which means the work isn’t about swiping harder or lowering standards — it’s about becoming the version of ourselves who no longer entertains people who can’t hold our story.

Simon didn’t break me. He simply showed me where I still needed to heal. And honestly? That’s a gift I didn’t know I’d ordered.