As Bonnie grew up, she often looked to her grandmother for help. Sheila played a huge role in her life as her mother was not around to do so. Sheila was the one that introduced Bonnie to witchcraft, due to this her father despised the relationship between the two. Sheila still looks out for Bonnie from the Other Side. However, since the Other Side's destruction, the two haven't seen each other again since their heartfelt goodbye scene. Sheila will always love Bonnie and is proud of Bonnie's accomplishments.
During the first half of season 1, Sheila told Bonnie about being a witch and helped her through it. At first, Bonnie didn't believe her, and joked about it with her friends. But, as her powers progressed she became scared, nervous and came to her Grams for help. Sheila agreed to help her, and taught her the witch craft ways and most of the do's and don'ts. Sheila used her powers along with Bonnie to open up the tomb beneath Fell's Church in which the vampires from 1864 had been sealed by Emily Bennett. Both found it draining, and Sheila told Bonnie to hold in there and keep going. Sheila later dies at that night from overload of magic leaving Bonnie depressed and as result, going through a personality change that made her more serious. She started to hate vampires, blaming them for her gram's death instead of the real reason; that her grams wasn't strong enough to do the spell.
"I would write... Dear Diary"
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In Resident Evil, she appears to Bonnie and tells her something is wrong with the Other Side and that something escaped. She tells her that the witches are afraid of what is happening.
In Home, Sheila briefly appears while Bonnie is on the Other Side. Bonnie insists that she, as the Anchor, can handle it if her grandmother passes through her and comes back to life. However, commenting on how she got to see her grand-daughter grow into a woman, Sheila declines the offer, stating that she found peace knowing that (when the Other Side collapses) Bonnie would too find peace. Bonnie and Sheila hug before Sheila departs, leaving Bonnie standing in the cemetery of Fell's Church.
In Nostalgia's a Bitch, while inside Damon's subconscious, Bonnie goes to see Sheila in hopes that her Grandmother can help her find Damon.
In I Was Feeling Epic, Sheila's spirit aided Bonnie one last time, during her greatest need, to save Mystic Falls from destruction via hellfire. Together, along with the other Bennett witch spirits, they successfully stopped the hellfire as well as destroyed hell in the process.
(Sheila opens her door to a confused and tearful Bonnie)
Sheila: Our family fled Salem in 1692 and relocated here. Our ancestors lived in secrecy for over 100 years. It's important that we still do.
Bonnie: Grams, everybody knows that you're a witch.
Sheila: They also know it's absurd. It can't be true. I'm just a cooky lady that teaches occult at the university. No one really believes. They just poke fun, and let 'em. Don't let 'em know the truth.
Bonnie: Where's the witchcraft. I mean, you've been talking history for two days...I want to get to the fun part.
Sheila: It's not meant to be fun. It's real and it's serious, and you must understand it before you practice it....aren't you late for school?
(Bonnie leaves for school and Sheila smirks while she drinks her tea)
(Bonnie frantically storms into Sheila's house and alarms her)
Sheila: A fine mess you've made honey. The witches told you there'd be consequences to bringing Jeremy back and you did it anyway.
Bonnie: I didn't have a choice. I love him and I couldn't let him go.
Sheila: I understand, but you cracked open a door to the Other Side. There's an old witch over, she took advantage of it, she took advantage of you honey. When you did that spell to send Vicki Donovan away, she wedged the door wide open, giving a free pass to anybody with unfinished business.
Sheila: That's Original Vampire business, not yours. I don't want you getting in the middle of that. I'm here because you upset the balance of Nature, and it's your duty to set it right. You need to close that door.
Sheila: (to Bonnie) You are stronger than all of this. I'm so proud of you.
Sheila: You think I was born yesterday? I know what you're doing. You cannot survive all these people coming through you and even if you could, when it's all said and done, you're still the anchor and when this place goes away--