In What's My Age Again?, Owen teases Anya about Dr. Chris,but after they don't work out, he finds Anya at her birthday party in Fiona's room crying and he tries to comfort her. Anya then kisses him, during her frustration and lack of judgment. The two lie down on the bed, making out and eventually have sex. Fiona and Holly J. are later disgusted to see Owen's Facerange status about hooking up with a girl in Fiona's bed.
In Idioteque, The rumor of Anya and Owen hooking up at Fiona's condo is spreading uncontrollably. Fiona is distraught thinking about Owen having sex in her bed to the point of saying she will get a new mattress. Holly J. and Fiona start searching for the person who had done such a disgusting thing as hook up with Owen Milligan. They feel bad when Anya says she is the "low grade" girl who would have sex with Owen. The girls also seem shocked and disgusted at the thought of their friend with the shallow neanderthal.
In Paper Planes (1), Anya and her mother argue a little over the fact that Anya only applied to TU (because she wanted to be near Dr.Chris), but Mrs.Macpherson softens when she realizes that Anya also had a hard time because of her cancer. Mr. Simpson alerts Anya that there is a slim chance that another university will accept a late admission. Anya is happy about this and prepares to fill it out. Because of all the work she has to do she bails on playing with Holly J.'s volleyball team. Holly J. is dismayed when Anya tells her that the night before she tried coke. She calms down when Anya promises not to do it anymore. Owen is upset when Anya can't hang out with him before he goes to his tournament due to her essay. He tells her that since working on the essay and the application probably won't have any effect, to call the university and tell them how she was helping her mother work through cancer which is why her admission was late. Anya is able to get a face-to-face interview with the Dean of Admissions. To say thank you to Owen for giving her the idea, she decides that they will go out the night before he leaves. During volleyball Owen brings his friends to play. He overhears Holly J. insulting him to Anya and sprays her with Gatorade. Anya and Owen go back to the club, but get into an argument over the fact that Holly J. doesn't like him. He tells Anya not to hang out with Holly J. anymore because she isn't good for Anya. He then calls Anya Holly J.'s dog. Anya walks away from him.
In Paper Planes (2), Holly J. is offended when Anya tells her what Owen told her the day before, and tells her friend to get over him, which she has a hard time doing and decides not to listen to either of her loved ones and still hold the relationships she has with them both.
In Take a Bow (1), when Anya mentions she now has a real date for prom at that it is Owen, Fiona looks uneasy; then smiles for her friend while Holly J. rolls her eyes and is upset that her friends are ditching the friend-date idea.
In Take a Bow (2), Holly J. tells Anya that she finally approves of her relationship with Owen.
- Holly J. is best friends with Anya MacPherson, Owen's ex-girlfriend.
- Both are friends/on good terms with Fiona Coyne and Imogen Moreno.
- Owen's younger brother Tristan idolizes Holly J.
- Holly J. was rivals and friends with Alli Bhandari, a girl Owen attempted to prostitute to himself.
- Owen had shown interest in two girls that mean a lot to Holly J.'s ex, Sav Bhandari. He had sex with and later dated Anya (Sav's ex) and tried to have sex with Alli (Sav's sister).