Damon: Damon brought you to an amusement park for fun. You both went on a big roller coaster together. Just before the drop, at the very top, he says,"(y/n)". Then he kisses you.
Stefan: It was Valentines day and you guys had been dating for a couple weeks. You open one of you presents from him and there is a piece of paper that has written in it "Turn Around". As you turn around Stefan grabs your waist and pulls you into a kiss.
Klaus: You entered the Mikaelson Ball, you step over to accompany you lover, Klaus. As you do he gets everyones attention. He gives a short speach about how beautiful you are and kisses you in front of everyone.
Elijah: You had spent the night over at the Mikaelson's, even though your relationship with Elijah has just nearly started. When you wake up you smell food so you rush downstairs. When you get there you find Elijah making breakfast for you. You jump into his arms and kiss him.
Kai: While you were stuck in the prison world together, it took you guys quite a while to get use to each other. Once you did, you guys had a very physical friendship. One day he took it farther and kissed you. You were surprised, but you kissed back.
Matt: It was your first date with Matt. He decided to take you back to your house. As you stood on the doorstep, he layed a gentle kiss on your lips and said goodnight.
Tyler: It didn't take long before you two were on top of each other and making out. It happened in his bed.
Jeremy: It happened in his bedroom whenever Elena wasn't around. The first time was just a week after dating.
Alaric: You stayed after school for "tutoring". You made the move when Alaric was bent over trying to help you with your work.
Enzo: He had his arms wrapped around you while teaching you guitar. You giggled and looked over at him after completing a little part of a song. He smiled back and leaned in. You starting leaning in as well until your lips met.
Kol: After making you a romantic dinner and setting it up, Kol brought you down to eat. Afterwards you cuddle on the couch. You look up at him and kiss him, believing its the perfect time.