Jillian O’Brien, of the Edenridge O’Briens as the family was usually keen to inform people before the events started happening, was born and raised in town. The youngest of five, she was always treated as the baby of the family, and she was happy to play the part most of the time, getting whatever she wanted in exchange for being her usual adorable self. She was enrolled in dance when she was going through grade school, and parlayed that into a spot on the cheerleading squad. Alison Davies was the pinnacle of everything Jillian was meant to be, and she was ready to follow that path. Until Ali was no longer there to light the way.
Jillian was crushed by the loss of an idol of Alison’s stature, but she pressed on. There were people on the team that needed her. She grew close with the other members of the squad as they pressed on in the shadow of Miss Davies’ demise. Lanie and Mei and Liv and Kat became like the sisters that hadn’t gone off to Boston College and other places that weren’t Edenridge for the moment. They helped deal with the passing of her father Shane to lung cancer in her sophomore year. It was tough, but they were able to move on. Until Charlie Decker happened.
Jillian didn’t even remember Charlie. Did they share a class at some point? They were both seniors, maybe freshman English? Anyway, she remembered his name after that. She remembered him shooting through the door of the barricaded science lab she and the rest of her Biology class were in, catching Mr. Lazovic in the shoulder and arm, and poor Matthew Carson in the head. Matthew didn’t make it out. Neither did Olivia Madden or Katherine Dunbar. Charlie got them both in the library. The last text in their group chat was about making plans for a weekend trip to Boston for some shopping ahead of senior year. Plans that never came to fruition.
Losing two of her best friends on top of her father and her role model took a lot out of Jill. It took a lot out of the squad. They all had their various breakdowns. Eventually, Jill was able to connect again, with a previous graduate of Edenridge named Michael Barrie who had come back following the tragedy to offer support. He escorted Jillian to the very subdued prom and eventually she moved into the Barrie’s house as Michael left his undergrad degree to stay in town with his new paramour.
However, Michael also had his own mask, and that was hiding the drunken lout he had a tendency to be at home. His own way of coping with the stress. Jillian joined in at first, as it seemed as good a coping method as any, but as things got serious and Jillian looked like she was going to join her fellow cheerleader in welcoming a child into the world, his drinking got worse. About 5 ½ months into the pregnancy, Jillian confronted Michael about what he was doing to himself, not wanting to lose another male presence to his own vices.
Michael responded by shoving Jillian down the stairs to the main lobby of the Barrie house. Michael’s sister Tamara heard the noise and called the cops. Michael was arrested, but the damage was done. Jillian lost her baby. Michael was sentenced to a year in prison. Jillian moved back in with her mother, who has been doing her best to comfort a life that Jillian is not certain she wants anymore. All the tragedy, the needlessly lost lives. Jillian doesn’t know what she did to deserve it. She still will come when called, she still responds to social responsibilities, but it was clear that losing baby Olivia (she wanted another to name Katherine) may have been the final straw.