Compliment and Insult at the same time?

It can be confusing for the mind when we hear a compliment with something within it that we are offended by. Something like "you're actually pretty clever"! Anyone here ever experience something like this?

I remember recently a man who used to say "you are a very clever boy" when I'd get something right. If I'm correct, one isn't a boy after the age of 12. So for him to be calling me a boy at the age of 31.

I remember a manager in retail once who used to do something like this. When one of his staff would do something good, he'd put his hand on their shoulder and say "just turn around there". Then they'd turn around and he'd say "well done" while giving them a pat on the back. So although the staff member is immediately aware that they've done something good, it's also kind of condescending. It's kind of like saying "you've risen in my estimation but you're still far below me".