I try to be a total gentleman when talking with providers during the session,

I think that's an individual preference sort of thing.  I had one escort start asking me about other providers.  She just seemed curious.  I think some escorts will gladly do sex talk.  It's fun and can keep them from getting bored with the same old routine.  I personally wouldn't enquire about specific clients, but I might ask them generally what sort of thing turns them on.  Although I guess I do that with sugar babes and not pros so much.

I'd be inclined to ask you for advice.  
In any event, there was a thread more or less on this topic just last week.  

And really not my style and should probably be avoided. Anything ,if you keep it light is probably fine. I like to talk about what's on the menu other then what we may have just done. What's she into.
And if a topic should come up where its filled with land mines then I'll act interested but I'll blow by it as soon as the opportunity should present itself.  
I find myself to be a pretty funny guy so I'll adlib shit, just to keep it jolly

-- Modified on 9/13/2023 8:39:07 PM

talk about other partners who taste bad.  Lol

When you walk in my door, there will be no question what the topic is 🤣 I do like to mingle our energies with some conversation. A little get to know each other but when hands, eyes and our minds are already engaged... things just flow so smoothly.  
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TL

how well I know the provider. Initially I’ll stay away from potentially sensitive topics while I learn what she’s comfortable discussing with me. With providers I know well, we might discuss just about anything, except real names are never used when talking about other providers and clients.

I had a woman who I seen often would complain about other clients. Finally, I told her I didn’t want to hear about her other clients. Started the beginning of the end. It’s like I have you here to pay attention to me. I don’t need to hear about X doing x and you think he’s a hill billy.

I love to hear humorous anecdotes about things that happened during sessions with other customers when something didn't go quite as right as it could.  Obviously, no names or identifying descriptions are involved, just something that a customer did, or she and the customer did together that they both found funny in the moment.  I've had many humorous moments with providers, so I don't mind sharing either.  It's a good way to run out the clock after our business is finished.

A few years ago I was in Jaco, CR, and brought a couple of Ticas back to my apartment. After some fun they were both holding onto my still-erect member and jabbering in Spanish. I don't speak the language really well but the gist of it was, "This is a really nice toy. Let's take it home." One of them jumped up and, giggling, ran to my kitchen, returning with a large kitchen knife which she laid up against my cock -- wisely, with the blade facing away from it. They were laughing insanely but you can imagine I kind of failed to see the humor, and told them, "If you want that thing to work any more, put the goddamn knife away."
So they did and the fun continued.

was with one of my regulars.  We hadn't been together in a month or two, and we were both really into the session.  We were in missionary, and what started as a slow, comfortable sliding morphed into some serious thrusting.  Everything was  going well until she started thrusting back, we were in sync, but I was no longer solely in control of the depth of each stroke.  Things became more urgent as we both approached orgasm, and on one long stroke, I pulled back too far and came completely out of her pussy.  She screamed, "Oh, no!!!!"  And I immediately shot back, "Sorry, I thought I was longer." She started laughing hysterically, and so did I.  We were laughing so hard, I lost my erection and missed the opportunity to slide back in and continue.  We took a break, and eventually started over.  This became a running joke for us in subsequent sessions.  

She was a French-Canadian stripper/bikini model with an amazing athletic body who loved to fuck. I got her to stand up against a floor-length mirror with her hot ass sticking toward me and we begin to fuck vigorously. As she got more turned on she began thrusting back at me so strongly I thought, "this girl is gonna put me through the wall!"
She went on to become the porn star Savanah Styles and married Lexington Steele. She also put on weight. But I'd still fuck her.

and will talk about the first thing that pops up.

The question pertains to spending time with a provider off the clock and hanging out as friends like going to events and dinner, after knowing each other for over a year and a half,  

Providers say to not ask them about the services they offer.
Well , most of us want to know what we are buying and being locked in by your no talking rule, clients have to play wackamole with many weird questions to try and figure out if you are the right fit.

on how to talk with friends you’ve known for over a year and a half?

Maybe the question is not lie clear,  

Sure, not everyone is a time waster but there are more than enough time wasters so that it has become a nuisance. As the push for legalization increases and various forms of sex work has gone "mainstream" i.e, OnlyFans/SeekingArrangements, there has been a massive influx of tire kickers and time wasters. My last ad got 50 responses within one hour of it going live, only 3 of those were legitimate clients. If you are a sincere client who actually wants to see a provider, you will take 5 minutes to actually READ their advertisement and a perhaps a review or two. Then you will not need to ask repetitive questions to "know what you are buying". A provider's time is just a valuable as a clients, and we do not want to waste our valuable time going over the same information we have already included in our adverts & profiles. Following booking/screening instructions is one very simple way to let a provider know that you are a not a time waster and most providers are happy to spend more time talking to you & answer addition questions AFTER you complete those steps. So maybe consider what you can do to put a provider at ease before complaining about a "no talking rule". You may not DM multiple providers a day, but providers are getting inquiries all the time. What can you do to stand out in a sea of horny texts/emails/phone calls?? -just my $0.02

You said a lot of words here but skipped over what I was talking about.

asking a stranger what topics I should or should not discuss with someone who’s a friend, whom I’ve known for a year and a half.  I know that person a LOT better than the stranger(s), who may not know my friend at all. I don’t think I’d be a very good friend if I hadn’t paid attention to what topics my friend likes or doesn't like to discuss, or if I wouldn’t have the courtesy to ask them if I wasn’t sure.

I have one provider highly rated on TER that I have seen a lot over many years. Not always but most time while we are talking she normally ask if I have seen anyone new and good. I suspect its to keep a eye on new competition. I have picked up some good provider tips over the years from her.  

I clearly understand your question but I also agree that it’s likely a personal situation between the provider and yourself - there are no set rules, and you will know her and your friendship best.