Absolutely. It can get damn confusing. Currently, I am "dating" my regular escort in the sense that more than 50% of the time, we go out to a show or to play tennis wo me paying her a fee. I still pay for sex, but that is an effort to stop the relationship crossing the line fully into real life, which I am not ready for.
I have had various line blurrings with at least a half-dozen other girls over the years. It can vary from a little extra time off the meter while she tells you about her rl issues, to shows, movies, dinners off the meter.
You have to try an figure out when you are being played, semi played, slightly played or not at all played. So it's always a risk. And I am not convinced they would shag you more than that "good girl" once they got a ring on their finger. They're all females at the end of the day and they all function in much the same way.
Like I said, be careful. One of my escort friends (who I still have dinner w once in a while) extracted a condo on Queens Quay out of a love-sick client a few years ago as the price of agreeing to marry him and quitting the business. He put the condo in her name alone before the scheduled marriage day. He's still single. She's still escorting.