I met a client like 3 times. Really enjoyed my time as this was dinner dates, was even filling sorry for him knowing his issues.

Then 4th time I initiated after he got quiet and I was in a city, wanted to make some money. So typical busy-ness excuse but we met.

Since then I had to initiate and each of this meeting is less and less exciting. Still enjoyable as he is educated and well mannered so will not reject the meeting but it feels...

I guess I somewhat hurrted his ego or I dont really know. Obviously he won't tell. Possibly once I put him down on earth when he was on a dreaming mode. Or we just simply lost the spark.

At this point it is hard to recall after time passed.

Thoughts on that type of situation?

Unpopular opinion : this is exactly why I'm not really fan of regulars and prefer having new clients every time. I feel that after 2-3 times seeing them, it becomes more and more boring so that if they text me again in the future to arrange another booking, I will typically ignore them not to see them again.

Don't get me wrong, they are some clients who are genuinely interesting and "entertaining" that you could see over and over again but these are relatively rare in my opinion. Plus, I also get that having regulars is comfortable (no security issues, you know what their expectations are, it helps when it's quiet, etc.) but I just feel that the "emotional" labour (if we can call it that way) gets more and more as you keep seeing them so I just prefer letting them go at some point.

Is it only me feeling that way or does anybody else feel the same ? 

Firstly, on their first (or even second visit you never know whether they will become a regular.
And the ones that specifically mention that they are looking for a regular girl (on the phone before you've met them) - well, they are not. you will see them once. They always say the same thing, hoping to get a better service or a discount.

Some clients are looking for the thrill of something new every time. And you have no control over that.
But there are plenty of clients who prefer to come back to what they know - so you are looking to win them and you can't tell who they are on first meeting.

I think you can increase your chances by:
1. having a really clean workplace and bathroom (I know mess/dirt does put some clients off from returning)
2. it's not the sexy things you do but everything else... such as being friendly and someone they can talk to.
3. if they become a regular, they will talk to you about their work, family, and whole life. So make yourself available as a good listener and allow time in the session for this sort of talk.
4. My own approach has always to be the most expensive WG around. And there are a number of reasons:

a)it puts off the guys who go visit all the cheap women - they are after quantity rather than quality
b) the men who visit you are less sensitive to price, and these can tend to be more likely to be regulars.
c) it's really hard to increase your prices. So, you might well be charging the same money in 10 years' time. It is much easier to start high - and you can always offer a sale or discount now and again.

Oh god, the ones who ask you "what will we do this time?" and constantly want edgier and edgier roleplays. It's like they are kink tourists and my bedroom is an all you can eat buffet.