Damon- he takes you to a bar you two drink and get to known each other

Stefan- he takes you for a drive in his car and you two go for a hike

Klaus- he takes you to an art museum. Comparing you to the most beautiful pieces of art

Matt- you two go to the movies. It was awkward  because you couldn't really talk

Jeremy- you go over to his house for a home cooked dinner. After dinner you play video games

Alaric- you two go for a jog. Not the most romantic but you enjoyed it

Tyler- your first date is actually at one of the founders day parties. He introduces you to his parents and shows you off. It was very embarrassing

Elijah- you go to a library together. You both love books so you check out the mystic falls library. When you got bored of it he showed you his personal collection of books. It amazed you