"endear"?

I'm used to read sentences like "endearing oneself to other people", such as "endearing herself to her friends", "endearing myself to my potential audience" and so on.
When I read this sentence, I got confused:
"...the bartender filled the bottoms of our glasses, emptying half the bottle in the process and endearing us to him for the evening."

Endearing us to him for the evening?? Making us love him by pouring us half bottle of wine?? And...the evening? What's this talking about?

"...the bartender filled the bottoms of our glasses, emptying half the bottle in the process and endearing us to him for the evening."

Okay. Let's start with the amount of wine the bartender dished out -- probably more than average. That's why the customers liked him so much, and that feeling lasted for the rest of the evening.

"Endearing us to him" is a bit odd in this context. I'd expect "endearing him to us," since it's hard to see how an act he carries out himself could cause others to become more beloved to him.