- Ally: "I haven’t been back here in a lot of time Stefan, this could be nice."
- Stefan: "If by “nice” you mean trying to stop our older brother killing a bunch of innocent people then yes, Ally, this is gonna be real “nice”."
- Ally: "Sheesh, I was just trying to see the silver lining"
- — Ally and Stefan bickering.
Ally first arrived in Mystic Falls in the "Pilot" after being called into town by Zach because of the recent murders commited by her brother, Damon. When he called her, he reffered her as "Aunt Allyson". Zack, having not been born during her ripper years, knew only the responsible and stable Ally that tried to stop her brothers from ripping each other’s throats out. He was, however, aware of her actions (though never speaking of it) and thus treated Ally with the same caution he extended to Stefan, but not as much as he expresed toward Damon, who he appears to be very afraind of.
Stefan was surprised to see her, as the two apparently had not spoken frequently since 1993, when Ally apparently expressed she felt that Stefan had given up on their brother. Stefan while offended had tried to calm her but she apparently left to do it herself, “as she always did”. The two weren't bitter about the argument, as Ally, had apologised later on, but the tow had differing opinions on their brother, as Ally still felt they could help him. looking around Stefan's age, decided to attend the high school with Stefan as his twin sister (rather than his younger sister, as she actually is). She found it hard not to look too surprised when she met Elena Gilbert at the likeness she shared with Katherine Peirce, despite having been warned about it by Stefan before meeting her.
Ally attended the party at the falls with Stefan, despite having not been invited, as she wanted to keep an eye out for Damon, to see if he would attack again, so she could find him and confront him. During the time waiting, Ally drank a few beers and was hit on by a slightly drunken Tyler Lockwood, who she politely told he might want to get a ride home. She was also later offered the option of trying out for the cheerleading squad by Caroline, who seeminly intended to use her to get to see Stefan.
After Vicki is found unconscious, Ally attempted to look for Damon before leaving for the Salvatore Boarding house, just in time to see catch Damon and Stefan at each other’s throats. She attempts, but fails, to intercept the two, but Stefan launched himself at Damon and they both went flying out of the window. As Damon continues to taunt Stefan, also trying to anger Ally she tells him to “knock it off” and stop “acting like a child”. Damon proceeded to throw Ally to the ground, provoking Stefan to run at him, however Damon just threw him against the garage with ease. He warns Stefan not to try an cross him again and Ally to stop trying to turn him into another Stefan, otherwise things would get more interesting.
- Damon: "If you think I don't know what you're trying to do you're sorely mistaken, and I'm slightly offended."
- Ally: "I'm merely trying to blend in as a typical Mystic Falls teenager, teenagers have hobbies."
- — Ally and damon bickering
Ally in-uniform
This led Ally to, rather than back down, per say, try to be “sneaky”. When she realized that Damon was using one of Elena’s best friends, Caroline, due to the scarf she was wearing when she was dropped off by him for cheerleading. Originally having been there to tell Caroline she didn’t want to join, she decided to try out for the team to keep close to her, a move that Damon saw right past, though that was half of Ally's point.
After practice, Ally approaches Tyler, who is with Matt, and asks if he was able to get a ride and that she was sorry she couldn't offer him one, resulting in Tyler snapping about "not being drunk". Ally meets Matt as he apologises for Tyler’s behaviour after he stormed off. He instantly reminds her of Joshua North, but she doesn't tell him that as it would be very creepy.
When Damon confronts Stefan and Ally after the game, Ally and Stefan tell him that things didn't need to be the way they were and that they knew that Damon had a soul in there somewhere he just had to want to find it. This prompted Damon to kill Mr Tanner, in a show of proposed irredeemability. This works for Stefan but not to Ally, who still blames herself for Damon turning off his emotions. When it becomes clear to Ally that Damon is mistreating Caroline, rather than "doing nothing" like Stefan she confronts him, eventually leading to Damon snappingh her neck to shut her up.
During this time, however Stefan and Zach pull off their plan to capture him. Ally is only persuaded to back off later on by his seemingly remorseless acts of violence in killing Zach and turning Vicki and allowing people to suffer for the fun of it. She didn't, however, give up entirely.
Things become awkward when Lexi Branson, Stefan’s friend, came to town to celebrate Stefan’s birthday, due to both Damon and Ally’s actions in the 70s. However, Ally swallows her pride and tells Lexi that she doesn’t expect to be her best friend, but that she wanted her to know that she regretted her and Damon’s actions and that she was sorry. Lexi accepted her apology, however it’s impossible to know if they could have ever got on, as Damon killed her later that night to cover his tracks.
- Stefan: "He says he’s gonna bring Katherine back, that’s why he’s here."
- Ally: "Well that’s a stupid idea, even for Damon and even if it were possible. Just all around stupid, across the board, really."
- — Ally and Stefan discussing Damon’s revelation.