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My rules for tipping don't change no matter if the server is a friend, family member of complete stranger...
If I like the place enough to go back on a regular basis I tip BIG, sometimes 25% or 30%. Soon they know me and I get the most awesome service and food bennies even when everyone else is getting crap service. In smaller places I've had owners bring out new dishes for me to try for no charge. Once the owner of a Thai resturant brought me some of what THEY were having for dinner and it wasn't even on the menu.
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