Without. Not only am I short, so 5in heels would get me no where near, but I also don't care. So he's a couple inches shorter when I wear heels. So what? (admittedly that rarely happens because 5ft and 5in heels are awful. The smaller the foot, the more the incline hurts). As long as a guy is at least an inch taller than me w/o heels, I'm happy... assuming I actually like him.
I measure without. I'd never let whether I'm taller than him or not, with/without heels, lead to my turning him down. If I turn him down and he happens to be shorter than me, that's unrelated to the rejection.
Lol who even does that? I sometimes think that, if a guy is still a bit taller or same height with me when I'm wearing heels, then that's the perfect height, but I'm literally fine with anyone who's about my height.