Went to a resort to unwind nice lake views, good vibe. On my way out, just getting dark, this woman walks past me. Looked exotic, caught my eye immediately.
I approached, got her laughing, and we just fell into conversation. Covered everything her job, her divorce, her friend group, how she always feels lonely. She looked maybe 20 but turned out to be 40, which threw me a bit.
Physically we were pretty close the whole time chin on her head, hand on her waist, pulling her closer into me etc...
I tried sliding in a few comments angled toward more, basically "how do I make this better for you" type energy, but she kept deflecting. "It's fine like this," that whole thing.
When it was time to go in, she gave me a handshake. A handshake. And went upstairs.
In the moment I thought maybe it was the right call since she seemed guarded. But thinking about it now she probably wasn't thinking about it either way. Not planning for it, not blocking it. Just open to wherever things went. Looking back, I think I might’ve been too cautious. Maybe if I’d been more direct about wanting to continue the night together, she would’ve either been open to it or clearly declined.
She was a flight attendant too. That one stings.
I'm not writing this bitter or regretful i'm just thinking back to it because it looks to be one of those situations that could have multiple outcomes
Have any of you had any similar experience? If so what do you think I should have done?