A lady I connected with online (not a dating site or similar) asked if I was willing to help with a web site. I said ok and we met up at a nearby late night restaurant. It turned out it was a porn site and she was a porn actress, wanting to have her own site instead of the exploitive one that she was then on. We had a nice conversation about all kinds of things including web development.
The restaurant was not fancy but she spent a while picking out the cheapest things on the menu. I was the one who suggested the meeting place and I inferred that she was having cash flow problems while I was working as a programmer, so I figured I should pick up the tab when it came. It was just the considerate thing to do. When I picked it up, she freaked out as if I expected something from her because of it. She left the restaurant in a big hurry and I didn't hear from her after that, oh well.
She was an interesting person, and attractive, and I didn't anticipate that reaction at all. I like to think we could have gotten to know each other better if I'd let her pay her own tab. Shrug, whatever.