Cute flats on a first date. Heels depending on the venue, your comfort level, the height of your date and the kind of date you’re having - if it’s a blind date. If you’re off to someplace fancy and the guy’s tall enough, heels would be okay as long as you don’t wobble while wearing ‘em. If the date is nice and lowkey, I guess it would be safer to go with a pair of pretty flats. If the date itself is a surprise kind of thing, go with flats. Malay mo magwalking tour of Manila pala kayo or something eh di napagod ka pa. :(