ok so i’m born and raised in hawaii. One important thing to get across, is that Hawaii people are very kick back, very chill.
if you see him again, and there’s a big chance you will because the islands aren’t that big – just, as we say, ‘chance um’. Just go for it.
be polite, a little flirty – say hi and introduce yourself.
or you could pretend to be looking for something – no doubt he’ll help you

Just buy the souvenirs, every body will love you.