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—hiccup haddock - he takes you to one of the many islands he's found and you guys just relax against your dragons and look at the views (+ the sunset if you go at the right time)
—astrid hofferson - dragon racing counts as a date right.. - well, she invites you to race (just you two) over the ocean and it's really fun when you spin around on your dragon
—tuffnut thorston - i think a pretty successful date would be going around pranking random people by leaving buckets above their doors so the water pours down on the person while they open it or just simply scaring them - it gives you both a good laugh and it's rather fun if you don't feel bad about it
—ruffnut thorston - she would do anything with you and think it's cute - so whatever the hell you want, even if it's just walking around berk and talking
—fishlegs ingerman - picnic in a place in berk that has a pretty view - he brought all your favorite food - 🥰🥰
—snotlout jorgenson - it would be dinner somewhere - whether it was in the great hall or somewhere else, it was kind of awkward - when he asked you, he pretended to be unfazed and a big man but you could tell he was hella nervous
