I think I insulted my daughter's prom date

by proposing twice that we'd pay for half of the expenses.  The second time he told my daughter that it was the man's responsibility, end of discussion.

That was last year (My daughter did not do prom this year because of a conflict.) and I am still feeling bad about insulting the boy (man) and about not paying (It was quite a bit of money).

Situations are different and people are different of course.  I'd still say it once that I'd pay for half.