Over the years, with a few regulars I've had the pleasure with, I got into arrangements where I'd release my debt to them in a lump at the end of the week/2 week/month.
They appreciated it for the fact it wasn't burning a hole in their purse/pocket. For the last one I actually made deposits to her account!
Only real issue was I kept the books, so to speak. With safe guards to be sure.
Certainly NOT for everybody or every situation but it worked for us.
I also tried a "money card". My account with her name (on the card). That didn't work out so good for reasons I won't get into.
My 2¢.