In All I Wanna Do, Tristan and Winston meet for the first time as roommates during their Paris school trip. Initially they don't interact much, because Tristan is primarily focused on being in a relationship with Miles Hollingsworth III, their other roommate. When they first meet, Tristan is caught looking at Miles shirtless to which Miles responds "Take a picture, it'll last longer." Embarrassed, Tristan claims that he was thinking about his girlfriend, to which Winston surprised asks if he really had a girlfriend. While in class, Tristan is trying to convince Miles and Winston that he is in fact dating Maya Matlin. He brings Maya flowers and Miles, knowing its an act, tells Tristan to kiss Maya. Tristan refuses, but Maya goes ahead and kisses Tristan anyways. Winston, seeing how disgusted Tristan is, sarcastically asks "Trouble in paradise?"
In Cannonball, Tristan goes missing after an argument between himself and his best friend Maya. When Maya discovers that Tristan has gone missing, she tags along Winston to help find him, even though Miles offered to go help initially. While looking for Tristan, Winston tells Maya that it is likely that they won't find him in such a large and vast city like Paris, saying that he might be floating in the Seine for all they know (implying that he's dead). This upsets Maya, most likely bringing back memories of her late ex-boyfriend who committed suicide. Winston responds by saying that girl tears are his kryptonite.
In This Is How We Do It, Winston states that there is no one at Degrassi worth knowing, to which Miles, looking at Maya and Tristan, says that there is probably one or two people he could like.
In You Got Me, Tristan is seen walking in the school dance with Winston, Maya, and Miles.
In You Oughta Know, Tristan and Winston are seen talking and laughing with each other at Miles house party. Miles interrupts, bringing an umbrella that Tristan ends up holding. They have a brief chat with Tristan saying that he likes Miles house because its very 'house wives'. Miles states that the reason it looks that way is because his mother is bored. Winston replies by saying that she's also hot. Tristan and Miles phones suddenly ring, with Tristan acknowledging that its the results from the basketball tryouts. Miles becomes visually upset when he realizes that he didn't make starter, but congratulates Tristan for making the team. He storms off saying "Screw this". Tristan, confused, asks Winston if it was something he said. Winston then responds with "Maybe, you never know with that guy". Tristan then heads off to see what could be wrong with Miles, leaving Winston standing in the rain.
Part of the conflict was in Can't Stop This Thing We Started when Winston told Zoë about him feeling jealous that Tristan is taking Miles. He also fights with him when he is hanging out with Miles and Tristan comes in and wants to play Just Dance. Winston and Miles talk about how upset he is that he is always with his boyfriend.
Degrassi: Next Class
In #RiseAndGrind the two play truth or dare with Zoë and Miles. Winston later talks with Miles about having sex with Tristan.
In #KThxBye, they are both seen comforting Zoë during graduation. They are later seen at the post graduation party at the Hollingsworths.
- Winston is accepting of Tristan's homosexuality.
- Winston knew Tristan was gay when he was 'dating' Maya.
- Tristan knew Zoë was gay when she was dating Winston.
- They are both friends with Miles Hollingsworth III, Zoë Rivas, and Maya Matlin.
- They both graduated as part of the Class of 2016.
- They were both sexually taken advantage of by Grant Yates.
- Tristan was statutory raped by him.
- He attempted to grope Winston.
- Winston warned Miles not to hurt Tristan's feelings.
- They were both members of the French Club.
- Both have dated the other’s best friend. Winston dated Zoë and Tristan dated Miles.