While it's possible that you could have gotten a "freebie" by not mentioning the money, it's equally as possible that she would have labeled you a cheapskate and would stop wanting to see you in the future.

You actually handled it rather well in my opinion, at least you didn't say "how much do I owe you?" Now THAT would have been stupid. lol It sounds like she is happy and you are happy, I don't see anything stupid when both of you got what you wanted.

I will confess I often go months without ever having a talk about money, in many cases I just ask if they need anything, but without asking for a specific dollar amount, when they invariably say "yes I could use some money" I give them whatever I feel like giving them and ask if that will take care of their needs until I see them again. That approach has been working for me, but there is no "one right way" to do this. As long as both parties are happy, who is anyone else to criticize?

You are stupid mate...  

but if your BFF Jabba says you played this one well, then I guess you played it well. Still doesn't take away from the first statement though...