The conflict between Connor and Luke began when both boys developed feelings for Jenna Middleton. Although Jenna was friends with Connor, she had previously been attracted to Luke earlier that year. When Connor saw Luke attempting to grope a clearly disgusted Jenna, he became upset and punched him in the face.
In Ray of Light (1), Luke approaches Jenna while she is handing out buttons for her anti-bullying campaign. She says that she didn't know that Luke cared about her since last time he kissed her and pushed her away. Luke claims that he has changed, and Jenna gives him a button. She asks how he has been since Campbell Saunders's death, and Luke says it has been weird on the team and that he has been praying a lot. Jenna responds, but is interrupted by Connor falling on the ground, which Luke laughs at. He jokes to Jenna about Connor, which offends her, and she tells him Connor is cooler than Luke ever will be. To prove her point, she goes up to Connor and kisses him on the cheek, causing Luke to leave.
In Ray of Light (2), Jenna finds out Luke has a crush on her from Becky, which makes her rethink her feelings for Connor. She talks to him about his crush on her, to which he responds by hitting on her and touching her rear. Her feelings for him fade quickly and their encounter is interrupted by Connor, who punches Luke and tells him to stay away from her. She gets mad because she thought Connor was different. However, she later makes up with Connor and tells him the date they went on was the best date she had ever been on. Jenna then gives him a gift and the two start planning their next date.
- Connor defended Jenna against Luke, which lead to the start of Jenna and Connor's relationship.
- Their love triangle with Jenna is considered unresolved.
- Connor punched Luke in the face.
- Both had feelings for and kissed Jenna but only Connor had a relationship with her.
- Both have a history with sexual abuse. Luke raped Zoë Rivas and Connor was molested by LoveQueen16.
- They were both members of the Degrassi Basketball Team, the French Club and the Degrassi Student Council.
- Both have had a conflict with Drew.