On The Vampire Diaries Season 6 Episode 17, Stefan torments Caroline. Watch The Vampire Diaries online to see him tease her about her inability to lose control even though she's humanity-free now. They verbally spar and then take turns trying to stake each other before being caught by a Whitmore student on campus during Spring Break. Stefan injures the student and Caroline heals her. Later, they dine on the co-ed before sleeping together.

Damon and Elena travel to 1903 with Bonnie and Kai to rescue Lillian Salvatore, Damon and Stefan's mother. She's been surviving on two drops of blood a week for longer than she can remember because that's all the blood which is left in her prison world. Damon and Elena find the Ascendant and Lily's special traveling companions whom she wants to take with her to the present day. Because Bonnie stabbed Kai, there is only one witch to get them there and not enough power to take them all. Kai is left in 1903 with six mostly desiccated vampires.

Alaric and Enzo join forces to capture Stefan and Caroline. They are unsuccessful. Jo tells Alaric to stop hunting vampires until their child is grown.