I love overnights and week end trips with my familiar friends! I like to talk about whatever HE chooses to talk about! I always tell him right away that if I ask anything he doesn't care to answer just tell me! That's pretty simple. I try not to pry too much, but I do enjoy good conversation. I don't share too many personal details either.....just general conversation. For example, I talk about family. but in general - no specifics and details.
I love to laugh, so if I am with someone who has a good sense of humor, that is a big plus over that much time.
If he wants to watch a movie, I don't think it is weird at all. HE is the boss during our time together (well, for the most part, anyway, lol). He is paying for that time, and if TV and movies is on the menu, that is fine with me!
Having a jacuzzi suite can be fun, too. Plenty of fun can be had while sitting in the hot tub with a glass of champagne. A leisurely dinner is always nice. Just like going on a "real date" with a true friend.
I don't think I have had any bad experiences, although I did get very homesick one time. I just hid that feeling, but it was tough for a bit. I can't think of specifics when it comes to "the good, the bad, and the funny....."
I did see a client who definitely over-shared, and I had to ask him to stop, because he was sharing details about others, and I felt it was none of my business.
But now I am rambling, so I will end by saying I really enjoy multi-hour sessions and overnights with the right person!