Day 9: Was the Wine Guy Flirting…? Asking for a Friend (a 55-Year-Old One)

Date: August 06, 2025

Author: Stacey Sylvester-Carter

 Some stories don’t come with a moral. Some stories just come with a smile—and maybe a bottle of bad orange wine.

A few weeks ago, I was home in New York and made a pitstop at a local wine and liquor shop with my friend Liz. We were standing there, studying the shelves like we were about to sit for an exam on wine varietals, when 'The Wine Guy' appeared. You know the type—confident, friendly, and mildly mysterious. He asked if we needed help, and we pointed to a bottle of orange wine we were considering.

He admitted he hadn’t tried it and didn’t know anyone who had. I decided to buy it anyway and he told me to make sure I let him know how it was. It was a casual exchange. I thought nothing of it.

But then, as I was at the counter checking out, he reappeared—out of nowhere—just over my left shoulder. He gave me a discount, smiled, and said again, 'Let me know how that orange wine is.'

According to Liz, his tone, body language, and entire energy were *flirt central*. Me? I’m 55 and apparently completely oblivious to flirting unless someone literally hands me a card that says, 'Hi, I am flirting with you.'

I later posted in the local Facebook group to tell the anonymous Wine Guy: definitely do *not* recommend the orange wine. (It was a hard no.) And just like that, I’m probably never going to see him again.

But here’s the thing: That five-minute exchange? It mattered.

It was one of those nights where I needed to feel something good. To laugh. To smile. To feel seen. Not by a man. Just... by life. And even though I still have no clue if he was flirting or just doing his job with flair, I walked out of that store lighter.

I’m eight months separated now. I don’t really know how to 'start again.' The thought of dating is… strange. Weird. Uncomfortable. I don’t even know what the rules are anymore. Am I supposed to download an app? Do people still meet in person? And if someone *was* flirting with me, would I even recognize it before they walked away?

The girls at work loved this story. They said it should be a blog post. So here it is: Stacey, at 55, unsure if the Wine Guy was flirting, unsure if she’s ready to flirt back, and learning that sometimes, a smile from a stranger is enough for one evening.

Maybe the real message isn’t about dating or decoding signals or second chances. Maybe it’s just this: We’re allowed to feel good again. To let joy sneak in through unexpected moments. To laugh with a friend over a bad bottle of wine. To notice someone noticing us, even if we don’t quite know what to do with it yet.

🎵 Spotify Pairing: “Good Kisser” by Lake Street Dive

Good Kisser • Lake Street Dive

One day, maybe I’ll be ready. Maybe I’ll flirt back. But for now? I’m just grateful for the smile.

And no, seriously… skip the orange wine.


“Because every chapter counts — even the ones that smell like orange wine.”
— Stacey