I headcanon Winter as straight.  He rarely falls for someone, but when he does, he falls hard.  He has learned to shut away his heart in fear that it will break at any moment 

Winter's dream date would be a walk through a snowy forest, ending in an ice cave or a glacier.

Winter would be scared of being to clingy to his dragonets, so he'd leave them alone to make their own choices most of the time, teaching them to be strong and independent.