Riley and Anya first interacted in the season 8 episode Bad Medicine when Riley asked Anya on a date and she accepted. However, Anya said that their kiss didn't "feel right". Riley turned out to be gay, and Anya was there to support him. In Seasons 10-11, Anya was often seen giving Riley relationship advice.
In Uptown Girl (2), Anya and Riley are looking at Mia's modeling photos with Mia, Holly J., and Chantay.
In Bad Medicine, he is seen setting up a secret hook-up with one of his old friends, Nathan, from camp in the Ravine. When Anya walks by, he suspiciously shuts the laptop, and runs after Anya, asking her out for a date. She accepts, and Riley attempts to keep his homosexuality hidden. Later on, they have a picnic and talk. Riley then leans in for a kiss. The kiss is very awkward and Riley makes an excuse to leave.
In In Your Eyes, Anya confronts him and tells him that she needs to interview him for some kind of Degrassi bachelor award. When she is interviewing on the morning announcements, she asks him if he likes blondes or brunettes. Riley awkwardly answers the questions. In yoga class Riley tells Anya that he is gay after checking out Zane Park, he also asks her to not tell anyone. Anya gets excited and then tells him that he totally likes Zane. Riley sort of denies it, but sort of proves it again after Anya tells him that Zane is actually gay. At the LGBT mixer at Above The Dot, because there are a lot of straight people there, Riley goes to the mixer but still feels he has to pretend to be straight. After going in to the club and seeing Anya, she suggests he go and dance with Zane.
Season 10In Tears Dry On Their Own (1), Riley tries to find someone else to hang out with. He walks up to Anya, and asks if they can hangout since they haven't in a while, but Anya tells him he can't because she has family responsibilities. Riley tries to negotiate, until Anya tells him that her mom has cancer. He is astonished, and asks if he can go to the hospital with her. Anya says okay but doesn't understand why. Later, after a football game Riley meets up with Anya and he tells her that he'll go to the hospital with her whenever she goes, because it'll be a good way to find a boyfriend, or something in that sense, Anya agrees. They go to the hospital, and waiting outside of the room they talk until Anya introduces her mom's doctor, Doctor Chris to Riley. After the doctor walks away Riley asks if she likes him, and Anya sort of makes it aware, she also notices that he likes him too. Riley tells Anya that he's gay because of his awesome gaydar abilities, but Anya thinks he's straight. They shake on it to see if they can prove their cases.
In Tears Dry On Their Own (2), Riley and Anya walk outside of school, and they talk about Doctor Chris. Riley begs Anya to let him go back to the hospital with him, because he only had about 4 crushes, and 3 of them came out, and the other one was Peter. Anya laughs and they begin talking about how they can find out if Doctor Chris is gay or not. They go to the hospital with a clipboard, they begin to interview the Doctor for their "relationship education" class. Doctor Chris lead them on that he was gay, by calling his old girlfriend by a partner, and that she was a doctor so he called her by doctor. Anya and Riley look at each other and ask other questions, Riley asks what he sees in a guy or a girl, and the doctor awkwardly answers that he tries to find the right girl, and never succeeds. Afterward, Chris asks why they're asking these questions, and Anya tells them it's for their relationship class, and Chris asks if they're in university, and Anya lies and tells him that they are, and that's their extra class. Doctor Chris tells them that they're lucky because that wasn't a class when he was at college; after Anya leaves, and Riley looks glum. She turns around and asks what's wrong, Riley tells her that he was just excited that he met someone he liked that doesn't go to Degrassi. Anya asks him to describe his dream guy, and he describes Zane. Later on, Anya and Riley are doing Algebra, Anya calls Zane to come over and help despite Riley's wishes, Zane comes over and helps, then leaves, but Riley calls him back and they talk.
In Still Fighting It (1), Riley takes advice from Anya. When Zane cancels his plans with Riley, Riley is upset and seeks advice from Anya, she tells him that he needs to find a way to make Zane see that he cares for him. They see Zane hang a poster for a LGBT event about homophobia and Anya suggests that Riley go, to try and show Zane that he is working on bettering himself. Riley plans to go, and does so. He goes and surprises Zane, who doesn't understand why he's there. Later, trying to make an impact and win Zane over even more, Riley gets the idea to follow the rules of Spartacus from Anya, and makes the whole team's shirts pink in the wash.In Purple Pills (1), Getting advice from Anya, he hopes to ask Zane out on another date, and make it aware that they're dating without making a public announcement. Anya gets the idea to have Riley and Zane sign up for the dance's King and Queen, or in other words King & King. Riley does so.
In Purple Pills (2), Riley debates with himself whether it's best to come out or not since he's being scouted by an Eastern college football recruiter. He talks to Anya about it and as he does so, Chantay walks up to him and says she's proud of him for nominating himself and Zane for King and King at the Degrassi dance. Riley doesn't understand at first and then Chantay tells him there's a campaign to get him and Zane voted King and King of Degrassi for the school dance. Riley is surprised and Anya tells him that the closet is officially bolted shut.In The Way We Get By (1), Riley wants to be a better boyfriend for Zane and asks for advice to Anya, she suggests him to go to Zane’s (ex-boy)friend’s art exhibit, instead of watching the game at home because boyfriends sometimes have to do things they don’t like for the sake of the relationship.
In Idioteque, Riley is seen with a new haircut, using one of the computers at Degrassi. Riley asks Anya if she was the girl that Owen slept with at Fiona's house. He then asks Anya if she wants to walk to class with him, which she agrees to.
In Extraordinary Machine (2), Riley is seen acting in the school play production. Anya originally went to see him perform.In Take a Bow (1), Anya invites him to prom (which he accepts) and he points out the strenuous parts of the military.
In Dead and Gone (2), it is mentioned that Riley will have to sit with Sav, Anya, Owen, etc. at Prom. Anya wonders if this will be a problem because Zane is also at their table and will maybe get awkward with him and Riley.
- Neither of them said anything in their first appearances.
- They both had a crush on Dr. Chris though only Anya dated him.
- Riley had a conflict with Anya's ex-boyfriend Owen Milligan.
- They both graduated in the Class of 2011.
- Anya was the first female to know Riley was gay. After Peter Stone, she was the second person to whom Riley came out.
- Their friendship is similar to that of Marco Del Rossi and Ellie Nash in that they started off as dating and later became best friends after the boy realised that he was gay.
- They were both members of the Degrassi Drama Department and the Yoga Club.
- They both made their final appearances in Dead and Gone (2).