Scott- He takes you to a hotel so you can lay down and watch your favourite movie together, and maybe have a little fun. :)
Stiles- He wanted to do something special for your first date so he took you to a drive in movie theater. You guys watched 'The Notebook'. It was one of your favourites.
Derek- He wanted to do something romantic so he took you out for dinner at your favourite restaurant. Afterwords he took you back to his place.
Isaac- He wanted to do something different and fun so he got his four-wheeler and took you mudding.