- Longest Night Howie Day
- Gravity Sara Bareilles
- Coming Down Dum Dum Girls
- Afraid of the Dark Ejecta
- Mad World Sara Hickman
5×04: Longest Night by Howie Day
~ Elena takes Stefan to their high school roof.
5×04: Gravity by Sara Bareilles
~ Elena tells Stefan she was never scared of his vampire side, then they almost kiss.
5×06: Coming Down by Dum Dum Girls
~ Elena thanks Stefan for following his instincts and protecting her from Tessa.
5×07: Afraid of the Dark by Ejecta
~ Stefan tells Elena about his nightmares and why he needs to kill Silas.
5×18: Mad World by Sara Hickman
~ Wind blows away a page from Elena’s journal, which is picked up and returned by Stefan.
5×19: Be What You Be by Angus Stone
~ Elena tries to distract Stefan with food while he’s quizzing her, then they are joined by Bonnie.
5×21: The Truth In You by The Garden District
~ Stefan and Elena try hitchhiking.
5×21: Bad Blood by Bastille
~ Stefan and Elena get picked up by the Traveler that helped them escape.
5×21: I’ll Be Honest by The Private
~ Stefan and Elena take refuge at The Mystic Grill when their moonlight rings stop working.