When your dating in high school, until how many dates is it cool your date starts paying for her own sh*t.
Most Helpful Girl
I think the first and second date you should ALWAYS pay, just because it makes her feel all pampered and it'll get you more dates... After that, especially if ya'll are hanging out at home and what not, I would start to ween her off of it OR just tell her "I don't really have the money to keep paying for you, I don't mind throwing in a couple dollars here and there and treating you occasionally, but..." And if she really likes you she'll probably respect your honesty! If she walks, then she wasn't worth you spending your money on in the first place.:P1