Should I tell my boyfriend his attitude towards money pisses me off?

Anonymous
So, he makes more than I do, and pays for a larger share of our dates than I, which is fair, but what pisses me off is, if I ask to borrow $20 or $50 here or there, he ALWAYS makes me pay it back, if it takes weeks, he still expects it.

What do I say to him? Such small amounts should just be let slide IMHO
Updates
+1 y
I should add he makes about 5x what I do!
Should I tell my boyfriend his attitude towards money pisses me off?
143 Opinion