As the only poster who likes to routinely pick up the tab, I feel compelled to emphasize a few things.

First, how one person (mis)spends his/her money is his/her own business. If you are uncomfortable having a friend pay for your dinner, pay for your own. That's pretty simple.

Second, paying for someone's dinner does not mean that you are trying to control them or that you have low self-esteem. I pay for a variety of reasons. Sometimes it's because I know my financials are more sound. Sometimes I pay to express my gratitude for friendship (I am not a gifty-type person and so this would encompass special occasion gifts). Sometimes I pay to get out of the restaurant quicker. Sometimes I pay just because.

Third, I don't keep track of who pays when. I know it shakes out and I feel like bean counting ruins the point of giving.

In any case there is a big difference between my desire to pick up the tab and your friend's and that is that this is my one guilty pleasure and I do it with cash in hand.

As a side note, whatever his reasons are for supporting his daughter in excess of the court order, it's his kid. Distance fathering has to be difficult and if the extra dollars his kid's way make him feel better about parenting, more power to him. I would do it differently (save the money to fund face-to-face visits), but I'm not him.