Caroline dreams of a childhood memory of her and her mother. She wakes up needing a glass of water and sees Damon attempting to write the speech for her mother’s memorial. He attempts to reach out to her but she shuts him down, and he tells her to be ready, tomorrow won’t be the worst day as everyone is here for her but next week.
Kai goes by Jo’s house, who has the head down the toilet, she believes she has food poisoning. Kai tells her that his body is rejecting magic, since he isn’t Luke’s twin. He reminds her that if he dies, as a leader, the whole convent will die, the “witch” prison will be destroy and releasing all the bad beings. He tells her he can absorb her magic and she can be. She before checks to see if he’s physically okay, and makes her decision with Alaric. He makes it clear that he will love her even without magic.
Damon day dreams about his own mother’s funeral. Refusing to make the speech and comforting a young Stefan. Stefan asks for his advice regarding Caroline. He tells her, that if he really thought she was the one, he wouldn’t be asking for his advice, that Caroline wants the real true love, and if he isn’t capable of giving it to her then he should break it off but not to chose today. At the funeral, Caroline attempts to speak to Stefan who prefers not to talk about it today. She gets the clue and asks to be alone with her mother. A drunk Tyler attempts to go inside the church but Matt refuses him to go in. Later on Matt decides he wants to become a cop and tells Tyler he should to. The funeral goes on, Caroline attempts to stay strong. Damon makes his speech as Stefan looks at Caroline :”Liz Forbes was my friend, in her last moments, she asked me to pass along a message to her daughter, but i cut her off before she could say too much. Told her she could tell Caroline herself. But she didn’t get that chance. Your mom wanted you to know how proud of you she was and she should be. You’re a beautiful, strong woman, generous friend, a bright light, you could see in the dark. She said you were extraordinary and you are. So was she. Liz was a hero to this town, she was a hero to all of you and she was the hero of me. Goodbye Sheriff, you will be missed.” Caroline sings a goodbye song.
Bonnie was able to get her powers back, put the ascendent back together and is about to cross over however, the eclipse disappears and she is projected back to 1903, in an unknown house. When she snoops around, she finds a journal speaking about celestial events and pictures of young Stefan and Damon. As Jo gives Kai her magic, Bonnie realizes that the eclipse and the celestial events are the same. She runs in between 1994 and 1903 to the cave. She does the spell but right before she is transported back to the present, a woman asks her who she is. As the transfer is complete, Kai looks healthy and he whispers her a secret. She is was not sick due to food poisoning but because of pregnancy. Alaric proposes, but she refuses thinking he is asking because of the baby but he admits, after Luke died, he bought the ring and was waiting for the right time. He shows off the ring and makes a formal proposal that she accepts.
Stefan tells Damon, it was a good speech. He admits to him that he failed Stefan by not making the eulogy at their mother’s funeral. Stefan tell shim that he was wrong about Caroline, that he really is in love with her. Damon tells him that today is the right day to tell her then. Caroline goes home and Elena comes to see her. She realizes that before she left, she talked about not feeling tomorrow and realized she would be flipping her humanity off, like Elena did. Elena quizzes her on whether Stefan telling her what she would have wanted to hear, would she still be contemplating turning it off. She doesn’t answer and as she cries she snaps Elena’s neck and leaves. Damon goes home, attempts to contact Elena and walks in on Bonnie making pancakes. They celebrate her return. She shows her the video of the house in 1903. He realize it’s his house and as she shows him the woman she saw. He’s surprised to see his mother.