Season 13In Summertime, Miles introduces Winston to Maya. Miles offers Maya and Winston some alcohol, but only Maya accepts. Maya drinks it, which surprises Winston. When Maya accidentally drops the bottle, Winston tells Miles maybe his father wouldn't be mad. When Miles's father pulls him away, Winston and Maya look in shock and concern. When Miles and his father are yelling inside the house, Winston tries to talk to Maya, which causes Maya to say Miles father yelling at Miles was awful, and Winston tells Maya it will be over soon. Soon, Miles comes out the house and suggests a "swim" and Maya and Winston try to convince him not to do anything stupid, but Miles jumps into the pool with his clothes on. Winston jokes telling Maya that she should "fish him out" but Maya leaves, saying she can't be around guys like him. Later, Winston and Maya go on the trip to Paris.
In All I Wanna Do, he laughs at Tristan when he tells him and Miles that Maya was his girlfriend. Later, him and Miles laugh at Maya and Tristan when Maya tells Tristan that they can't pretend to be a couple anymore. When Miles suggest that Tristan and Maya kiss, Winston does a kiss gesture, and they both laugh again when Maya actually kisses Tristan.
In My Own Worst Enemy, him, Maya, and a lot of other students look at Madame Cliquet when they don't understand what she is saying.In About A Girl, Maya tells Winston that he needs to talk to Miles for her. Winston thinks Maya wants him to tell Miles that Maya has a crush on him, but Maya denies it. Maya then tells Winston to tell Miles to stop making out with Zoë so much, but Winston tells Maya that if you ask Miles to stop doing something he would do it twice as hard. When Madame Cliquet teaches the class about petty crimes, Winston tells Maya that maybe she should do one herself.
In Cannonball, Maya first walks in on Miles and Winston shirtless, and Winston covers his nipples. Maya asks them where Tristan was and Miles tells her that Tristan had left before him and Winston got up. When Maya complains that Tristan could be lost, Winston asks her if he could have Tristan's espresso, which Maya ends up giving him. Maya then says she has to find Tristan and Miles suggests she take someone with her so she wouldn't be lost as well. Maya chooses Winston to come with her and Winston complains why he had to go and not Miles, and Maya replies that the last thing she needs is a guy like Miles. Miles throws Winston a shirt before him and Maya leave. Later, they are at the Eiffel Tower searching for Tristan but are unsuccessful. Winston tells Maya that they need a better plan but Maya says they don't and that Tristan would be there since he was bugging her to go to the Eiffel Tower all week. Winston tells Maya that he thought she knew Tristan had tickets and tells her some places Tristan could be, like on a train to Belgium, which makes Maya cry. Winston sees and tells her that girl tears are his kryptonite and assures her that Tristan is okay. Winston soon suggests that they need Miles, and Maya finally agrees. Soon, they walk in on Zoë and Miles. When Miles tells Maya that he knew she would come crawling back, Maya says she can't do it and almost leaves. Winston stops her and convinces her to ask him because it was night and Tristan was still gone. Maya then begs for Miles to help her and they leave Winston and Zoë. Winston later watches Maya and Tristan's presentation on crime and punishment.
In Honey, they laugh at each other after Madame Criquet tells Winston in front of the whole class not to wear vulgar t-shirts.
In Unbelievable, Winston tricking Maya to see Miles sing a song to her to apologize to her.
In Sparks Will Fly (1), Maya and Winston are seen with Miles and and he is warning them when Zig is coming.
In Believe (2), Winston is standing right next to Maya and Miles when they were about to kiss.
- Winston's first line was said to Maya. -- "It's Winston. Winston Chu."
- Maya used to have problems with Winston's friend Zoë.
- Both have been sexually harassed.
- Maya dated Winston's best friend Miles Hollingsworth III.
- They are in the same grade.
- They both went to Paris over the summer.
- Both have had conflicts with Miles over his relationship with Maya. Miles wanted Winston to lie under oath about his kiss with Zoë Rivas to protect her feelings and Maya has had relationship drama with Miles because of this lie.
- They both wear glasses most of the time
- Both have dated a Hollingsworth. Maya dated Miles and Winston dated Frankie.
- They were both members of the French Club.