|Intimacy Level||Ex-boyfriend and Ex-girlfriend|
|Started Dating||Between Degrassi Takes Manhattan (923) and What a Girl Wants (1) (1001)|
|Dating Status||Broken up in Breakaway (1) (1003)|
Season 10In What a Girl Wants (1), Bobby and Fiona are walking through the hallways of Vanderbilt when Bobby tells Fiona he got her the chance to redesign their uniforms. At home Fiona is working on her designs and Bobby tries to hook up with her. She refuses, so he forcefully grabs her arm. When Fiona screams in pain, he apologizes. The next day he tries again and when Fiona slaps him, he hits her back and gives her a black eye. Days later, she's hiding from him at a party and putting on makeup to hide her bruise.
In What a Girl Wants (2), they make up and Bobby saves Fiona from some criticism from Tinsley's father. When everyone has left, Fiona is making a meal with her family and walks in on Tinsley and Bobby kissing. She stays home from school and Bobby visits her, so she confronts him about what she saw. He gives her a weak excuse and she kicks him out. When she's supposed to go to a dinner with the Beckronridges, she keeps faking sick, and Declan calls her out. After he leaves, she breaks down and shatters a snowglobe Bobby gave her. While videochatting with Holly J, she almost tells her what happened with Bobby but is interrupted. The next day, Fiona still doesn't want to deal with Bobby, but he tells her Tinsley was a one time thing. Bobby's phone rings, and when Fiona snatches it, it turns out to be Tinsley texting about hanging out that night. Fiona tries to end the relationship, but Bobby knocks her down the stairs and refuses to let her end it.
In Breakaway (1), Fiona hides from Bobby on the roof of Vanderbilt, and is called by Declan to get off the roof. She immediately heads home, enhances her black eye with makeup, takes a photo, and posts it on Twitter. When Declan sees them and tells Bobby to leave his sister alone, Bobby denies everything, calling Fiona a nutcase. When Declan goes to see Fiona and she explains she darkened the bruise so it would show up on camera, he refuses to believe that Bobby actually hit her. Holly J. convinces him to believe Fiona, who shows him the bruises on her leg. Afterwards, Fiona buys a ticket to Toronto to see Holly J. Her mom eventually finds her there and convinces her to sue Bobby for assault.
In Chasing Pavements (1) After Fiona refuses to accept a $100,000 settlement out of court, Bobby goes to court with Fiona. Bobby's lawyer questions Fiona and makes her admit to enhacing pictures of the bruise Bobby gave her on her eye. At first it appears that he is about to win, however, when his current girlfriend Tinsley admits to being slapped by him, he is found guilty and Fiona wins the case. He is then advised to take anger management classes as well as owing Fiona $250,000.
- Start Up: Before What a Girl Wants (1) (1001)
- Broke Up: Breakaway (1) (1003)
- Reason: Bobby was abusive towards Fiona and was also cheating on her with Tinsley.
- They were one of the four abusive relationships on Degrassi, the other three being Kathleen and Scott, Rick and Terri, and Bianca and Vince.
- Fiona is the second character to take her abuser to court. The first is Paige Mickalchuk to Dean Walton, though Fiona is the only one to win her case.
- Bobby tried to initiate sex with Fiona.
- Bobby was cheating on Fiona with Tinsley Wharton.