[S6E18] I Never Could Love Like That
On the road to Whitmore, Damon tries to prepare his mom to talk to Stefan and bring his humanity back. She states that she overheard Damon and Bonnie talking about the cure. She knows he's afraid he'll lose Elena if he gives it to her. He tells his mother that she needs to give a performance of a lifetime because she claims that she wasn't coming back to America for Stefan and Damon like he thought.
[S6E18] I Never Could Love Like That
With Stefan, Lily tells her she's a ripper like him. She pours on the motherly warmth, telling Stefan the story he wants to hear about visiting him the day of her funeral. Damon watches as she reacts the sweet sentiments he fed her earlier. She promises never to leave him again. It works. He turns his humanity back on and hugs his mother with tears in his eyes. Stefan takes a few moments to contemplate all the killing he's responsible for then resolves to go find Caroline.
Elena tells Damon she was jealous when she heard about Jo's pregnancy because she always wanted a family and knows it's never going to happen not that she's a vampire. Damon asks how she could feel if things could be different, but doesn't elaborate.
They get an urgent call from Jo. She says they have to get the ascendant back from Lily. She explains that long ago Lily met a group of heretic witches who could siphon power like Kai. She turned them, and as vampires they always have power to siphon, so they're both witches and vampire, and ruthless. They were coming to kill the Gemini coven when the coven stopped them and sent them to the prison world with Lily. "Imagine Kai with the bloodlust of a vampire, now imagine six of them," Jo says. So Lily wasn't sent to the prison world because she killed 3,000 people, she was just caught up at the wrong time with the wrong people.
Matt hated vampires, hybrids, and all the supernatural beings that came to Mystic Falls as he blamed them for his many problems. However, in reality, Matt's problems likely started the day their dad left him, and he felt like he had to take care of his mother and sister (and couldn't rely on anyone else).
This, in turn, explains Matt's more serious and reserved personality, as it seemed like he had to grow up quicker than his friends (which partly led to his distance from the rest of the gang). He never seemed to have time for fun and was always left behind by major events in the town.
Although Matt proved to be a good guy, there were often times when he showed that he had a terrible jealousy streak and could be extremely immature if his feelings were hurt (as evidenced before Elena even started dating either Stefan).
His invisibility saved him from trouble most of the time because he could easily have ended up the same way as Tyler and Jeremy. Being normal also helped reduce the intensity of the action in the town, as he was the best example of what a normal person's life in Mystic Falls looked like. He became the human face of the show.
Matt had been through so much by season 8 that he became impervious to pain. Having been abandoned by his father at a young age, lost most of his family, and several of his friends, Matt felt like his life in Mystic Falls had been a wreck.
However, he grew up quickly and learned to fight through pain and loss, taking most of it in without talking to people. Losing both Vicki and his mother hurt him the most. When he talked to their ghosts convincing them not to join the dark forces, he expressed the deep love and care he felt for the family that he couldn't tell them when they were alive.
He had lost the side of him that cared more, using his hatred for vampires as the excuse for hurting everyone. In the end, he seemed to be jealous of the rest of the Gang because they actually had a life and attention that he never got.