Steve, you are a fine writer. I always enjoy reading your posts. As I read this post, I saw a few things I remember my Dad doing as well.In my case it was my own father. There is a line between being frugal and being cheap; he crossed that line years ago.
Some of it was seemed fairly routine, such as sneaking food into the movie theater. Usually by putting candy in my sister's toy purse so that he could feign ignorance if caught. And as I got older he started lying about my age so he only had to pay for one adult ticket.
I Remember one time when I was 14 he had taken us to Universal Studios, but of course he said that I was 12 for the cheaper ticket. Once inside there was a stage show where they asked for a volunteer from the audience, specifically they wanted a young volunteer 12 or under. My Dad got angry with me for not raising my hand to volunteer and said I was going to "get us caught" for buying me a child priced ticket. Like the the girl at the ticket booth was secretly following us around looking for clues that I might not be the age my Dad claimed.
I was talking to my sister a few months back and she was telling me that my Dad had taken her out for dinner along with several other family members. He offered to pay because he gets "cash back rewards" on his credit card and he had a coupon. My sister noticed that after presenting his coupon and getting the discount he very nonchalantly slid the coupon under a napkin, waited until the wait staff had walked away and then put the coupon back in his wallet. She mentioned that the restaurant is supposed to keep the coupon after he uses it. He replied that this particular restaurant frequently forgets the coupon and that he has used the exact same coupon a half dozen times already.
This reminded me of someone who once told me that using a coupon at a restaurant is being frugal but calculating the tip based on that reduced amount was being cheap. While I was curious about how my Dad calculated the tip I was afraid to find out.
I am not rich by any stretch of the imagination, but I have promised myself never to be cheap and have tried to be generous with my money even when the budget suggested otherwise.