> What kinds of things are you paying for, though? Consider there's a subtle, unintentional message if you insist on paying for their $20 burger and drink: "This $20 is a big deal to you, but not to me." Unless they are dirt poor, they can probably pay for themselves for most things.

I mean if you are stubborn enough you'd find anything innocent to be malicious but I'd wager most people would think nothing of it unless you do it every single time and also refuse reciprocal offers