Ask me out on real life dates. Lunch, dinner, a weekend away.
Do any of you ladies ever agree to this?
I have done coffee, lunch and dinner, I wouldn't do a weekend away or any intimacy for free, providing I like them, they are good company, they are one of my regulars and they pay for everything on the date then I'd consider it, absolutely. I'd want to have seen the person on a paid basis though for a good 10-15 times before I would consider this though to gauge what they are like.
I've had a few good meets like this and it has worked well with 2 or 3 of my regulars, you have to watch that it doesn't become too often and I make this clear before agreeing.