Not at a massage place, but I've been a regular with a number of WGs.
One became my semi-girlfriend after I think 5-6 months of bi-weekly visits. She even left the business when we were dating and I stopped seeing other WGs. We had GFE sex on a regular basis but our personal circumstances wouldn't allow a long term relationship. We're still friends and I see her every few years when I visit Hong Kong.
A more recent WG who I see on a weekly basis and have for the past 3 months, well her performance has decreased substantially. Partly because she's already jaded by the business and partly because she just sees me as guaranteed income so she stopped caring about performance. I keep returning to her because she has the perfect face and body that I wish I could find in a girlfriend.
I'm also friends with a mamasan at a different place and she treats me very well by telling her girls what I nice, handsome guy I am and to treat me better. She's the girls' boss so they're supposed to listen to her but that's not always the case.
Spending more money or consistently giving more tips can make you a favourite, but you'll never know if the girls like you because of your personality or because of your money. (At my job my boss has consistently told me to treat our business clients who purchase more better, regardless of how bad their attitude might be. Money can be power in business but that doesn't mean that I have to like them.)
So to answer your question, being a regular can be either beneficial or make no difference. Ultimately it's up to the girls' to decide.
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