I am 5’3″, and I dated one boy who was 5’10”. I wore heels on the first date, and I could tell he was uncomfortable with them. I was uncomfortable with the height difference without my heels.
I wear heels on dates because I feel more confident in my appearance when I’m wearing them. I would be very offended, though, if I didn’t wear heels on a date and the boy made a big deal about it. I’d dump the boy in a heartbeat, actually… total antithesis of what I’m looking for.