She arrived in the village in summer 1999, and instantly came across as the tomboy of the Reynolds family. Ollie got herself into a lot of trouble in autumn 1999 including various scams with Zak Dingle and getting drunk, leading to Mandy Dingle getting sent to prison for three months. Ollie was convinced her parents didn’t care about her because they were always working, and ran away from home in 2000. She was hiding out in the Sugdens barn. After returning home, Ollie was shocked to learn about her fathers affair with Lady Tara Oakwell. She hated her parents even more, and continued to be led off the rails by Cain Dingle. Villager Seth Armstrong was mugged in 2000 by 2 young girls Mel and Julie. Ollie knew them and had them arrested by Angie.
In 2001 she continued to fall for Cain, and they got closer. Ollie was very unaware that Cain was only after her to get at Angie. Ollie even slept with Cain, and when the truth came out about why Cain was chasing Ollie, she left home and moved in with the Daggerts. Ollie kept getting closer to Danny, and tried to repair her relationship with Angie. Eventually Ollie moved home. But in September 2001 seven teenagers, including her older brother Marc were involved in the hit and run of their head teacher. At first the gang tried to hide their involvement, but Ollie broke down and revealed all to Danny. Marc confessed and the others were all taken into custody. Marc was sent to prison for a year, and Ollie was devastated. Her friendship with Danny continued to grow, although Latisha speculated that Danny might be gay.
Eventually Ollie started dating Danny and the relationship got serious. As the months went on Danny and Ollie became more and more serious. Ollie was devastated when, while she was away at her father and Tara's engagement party, her mother was killed in a car crash, caused by Ollie's one time boyfriend Cain Dingle. The pain was made even more worse by the fact that Ollie had fought with her mother over Cain before Angie's death. After his family left the village Danny moved in with Ollie and Len, into the Reynolds home. But later Ollie moved out as Chris Tate tried to buy the house for a development he was planning.
In October 2003, Ollie left the village and moved to Manchester to go to university.