Drew developed a crush on Fiona in Season 10, as did his step-brother Adam. Drew was eager in his attempts to win Fiona over, but reluctantly backed off when he realized that she was more interested in Adam. After Fiona's relationship with Adam ended, she and Drew lost contact with each other. In season 12, they were reunited when they were both excused from gym class one day, and teamed up on a health assignment Darryl Armstrong gave them to complete for the following class. They later became roommates for a while until Drew decided to move back with his parents and go back to Degrassi.
Season 10In Umbrella (1), Drew and Adam are working on the food drive at Degrassi when Fiona enters. Drew convinces her to help out with the drive to fulfill her community service hours that are required (convincing her by saying that in doing something else, she may have to wear a hairnet or change an old man's diaper). She agrees, and throughout the rest of the episode Drew tries to win over Fiona's affection, only to be shot down every time. Later in the episode, Adam convinces Fiona that Drew's a nice guy, he's just nervous around her. Fiona appears to give Drew another chance.
In Umbrella (2), Drew and Fiona are seen packing food in the boxes. After the canned food drive is done, Drew approaches Fiona at The Dot. Fiona tells him she’s confused by the two brothers and doesn’t understand why Adam was so upset, since he’s always so sweet. Drew realizes Fiona doesn't know that Adam is physically a girl, and keeps quiet.
In Underneath It All, Drew attends the seniors' party at Fiona's loft.
Season 12In Closer to Free (1), Fiona attempts to skip gym class and look for a new roommate by telling Mr. Armstrong that "it's her time of month". To Fiona's dismay, she is given a health assignment to complete by the next day. Seeing that Drew is also trying to complete the same assignment, they split the work. The next day, Drew forgets his part of the assignment. Fiona is angered and tells Drew that he has to stop blaming his concussion for all of his problems.
In Closer to Free (2), Fiona walks out of class to be bumped into by Drew while he and Bianca help pick up her flyers. He wishes her luck on finding a roommate and makes a remark about her being a witch. Later on, she is seen showing Drew her apartment saying that they'll have to pay 50/50 and lays down some rules.In Rusty Cage (1), Fiona and Imogen are having movie night, and Drew quickly interrupts their romantic evening. Fiona begins yelling at Drew about the apartment being messy. Drew points out that the apartment was messy before he moved in. The next day, Fiona and Imogen come home to find that Drew has cleaned half the apartment.
In Rusty Cage (2), Fiona is first seen making a list in class. When Imogen walks in and asks what it's for, she shows that it is "ways to get back at Drew". Imogen doesn't understand why Fiona won't just clean and Fiona is too stubborn to do so. Back at the condo, Drew walks in on her crying and she reveals that she has never cleaned in her life and has always had help. She tells how overwhelming it is losing all her money and being completely on her own and Drew says the change is new to him too. He says he'll teach her to clean in no time and they'll get through it. Over time, the condo gets cleaner and she comes out of the bathroom. He asks if she got the clog out of the bathtub and she tries to get out of doing it but sadly completes the task. She thanks and hugs him for everything before dropping the hairball in his shirt as revenge. She pulls it out for him and the two end on good terms again.
In Sabotage (1), Drew is at work when Fiona comes up to him with a meal and tells him that it is a bribe so that he can stay away from the condo for the night so as to avoid Katie she then leaves as Dallas arrives.In Building a Mystery (2), he walks into Fiona's condo and almost sees she and Bianca trying on the wedding dress, angering the two girls. Later, Fiona bids on the 7 tickets to Las Vegas, which are to be used for Drew, Bianca, and 5 friends to have their wedding in Vegas. Bianca then tells Drew to write Fiona a check so they can pay for the purchased tickets. Degrassi: Las Vegas, Fiona helps Drew and Bianca practice for their wedding ceremony and wedding vows. On the plane to Vegas, Fiona and Drew, along with Imogen and Adam discuss the wedding vows and then she watches Drew has he tells Katie about the wedding. At the wedding, Fiona watches Audra scold Drew and Adam for lying and going to Vegas and going through with the wedding. Later, Fiona, along with Adam, Imogen, Audra, Mo , and Marisol help Drew perform I Can't Help Falling In Love With You for Bianca. Then, she attends Drew and Bianca's engagement party.
In Karma Police (1), Fiona prepares microwavable food for Drew, but then he tells her that he needs to move out to be with his family. Fiona is very upset that he's leaving and questions him on how she'll pay the rent without him there and he tells her that he paid that month's rent. He then goes upstairs to pack and leaves Fiona heartbroken and angry. Then she goes on Twitter and complains that her roommate (referring to Drew) told her he's leaving with a day's notice and starts searching for a new roommate.
In The Time of My Life, when Fiona and Imogen fight, Fiona angrily walks over to Drew and Bianca and starts dancing with them.
- They both have been held back a grade.
- Fiona is good friends with Drew's ex-fianceé, Bianca.
- Drew is good friends with Fiona ex-girlfriend, Imogen.
- Fiona dated Drew's stepbrother Adam.
- They have both been jumped by a gang.
- They lived together.
- They were seen in the season 12 opening credits together.
- They're the only ones that call Imogen, "Immy".