"Drew? He's a cocky little bastard. Someone needs to remind him that he's just a rookie."
Drew and Owen had a rough start when Owen helped Riley Stavros tape a naked Drew to the school's flagpole, as well as several other horrible instances. They made up sometime between Winter and Spring break of 2010 and started a mutual friendship.
Throughout most of Season 10, they were enemies, due to various feuds, such as Owen and Riley hazing Drew, Owen and Fitz bullying Drew's brother, Adam, Owen trying to buy sex from Drew's then-girlfriend, Alli.In 99 Problems (1), Owen asks Riley if there's a problem with Drew, and they agree to help each other out, and make Drew pay for all the blackmail he threatened Riley with.
In 99 Problems (2), Owen helps Riley tie Drew to the flagpole and strip him of his clothing. They walk past him when the bell rings and laugh, giving each other a high five. A few moments later, Owen is seen standing next to Riley when they and the whole team get confronted by Drew's uptight mother. Owen is nervous because he was part of the reason why Drew was on the flagpole, but he stayed calm.In My Body Is A Cage, Owen teases and abuses Drew's younger brother, Adam, for being an female-to-male transgender. Drew ends up fighting Owen and Fitz, but loses.
In You Don't Know My Name (2), Owen thinks it is a stupid idea, but he teams up with K.C., Drew, and another football player to help Drew win Alli back by saying a poem. When it doesn't work he feels embarrassed himself and calls it stupid, then he laughs and leaves.In All Falls Down (2), Owen is first seen in the background during Drew and Alli's fight. Later when Alli is in the hallway crying he shows up and asks if she's seen Bianca. She replies saying that she is probably hooking up with someone elses boyfriend. Owen sees that there is something wrong with the pretty girl and asks her what it is, knowing she was with Drew. She tells him about Drew and Owen replies saying that people would pay big money to hook up with a girl like her. When she asks how much he says a million dollars but he only has 50. They then decide to meet in the boiler room after he gets his wallet. Then, in the boiler room, he shows her the 50 dollars but she says this isn't about money. Owen seems excited by this and goes in to kiss her. She backs from him and asks if they want to talk. He replies saying that this isn't how it works and proceeds to kiss her. Alli gets a little angry and says don't touch me. Owen tells her that her boyfriend just cheated on her and that she's a tease. Then Drew comes into the scene telling Owen to stay away from her. They come face to face and look like they may begin a fight. Then Owen just leaves the room saying it's so not worth it. He is last seen, after the lockdown is announced, telling Audra Torres that Drew is in the boiler room, probably having oral sex.
They both put all their past behind them in Season 11 and became friends.Should've Said No (2), he and Julian are extreme fighting during the dance. The decide to teach Drew, and in twenty minutes Drew is able to beat Owen.
In Mr. Brightside (1), Owen is the lookout for the fight club and warns the other guys that Coach Armstrong is coming. Later, he is seen in class with Drew and Julian discussing Drew's fight with Mo. When they go back to train in the weight room, they discover that Mr. Simpson has put a lock on the room and supervision is now needed.
In Mr. Brightside (2), he, along with Julian, tells Drew about an underground MMA fight. He goes there with Julian, but they both decide that it's too dangerous. Drew then shows up and challenges a man to a fight. When Drew gets knocked out, he runs into the cage with Julian to try and wake him up.
Season 12In Come As You Are (1), Owen attends Drew's party, and records Drew saying that he had sex with Katie and drinking a beer in a trophy. After Drew blacks out, Owen helps him up, and shows concern for his friend.
- Owen Milligan and Riley taped Drew to a flagpole naked.
- Owen had an attraction to Drew's girlfriend at the time, and was forcing himself onto her for sex in the boiler room until Drew stopped him.
- When Owen found out Drew's brother, Adam Torres, was transgender he threw Adam through a glass door then beat Drew up with Fitz after school.
- Despite their intense conflict during the first semester of their junior year, the two are good friends now.
- However, sometimes Owen will still make rude or sarcastic remarks to Drew.
- They are both friends with Mike Dallas, Julian Williams, Mo Mashkour, and Jake Martin.
- They both had a conflict with Riley Stavros.
- Both have a LGBT younger brother, Drew with Adam and Owen with Tristan.
- Drew became friends with Owen despite the latter never apologizing for throwing the former's brother into a door or trying to rape Alli.