Most Helpful Guy
Depends. I like to be at least an inch or two taller than the girl. I am just about 5'10'' so if the girl is like 5'8''-5'10'' it is kind of iffy. If we are going out and doing something new then perhaps it is fine, but if we're just going to get something to eat then there really is no need. Heels are supposed to make your legs and butt look better, but If I am already dating you there really isn't much of a need for that as I am already obviously attracted to you. However, if you are going out with friends and trying to get attention, yes heels would help a little.
Oh, and if you do choose to wear them, do not EVER complain about them. It is your fault for choosing to wear them, if they are uncomfortable bring something else to wear, we don't want to hear about it haha.