During the rock climbing challenge, Heather pulls a prank on Gwen that causes her to lose her skirt while climbing the mountain, leaving Gwen with her underwear fully exposed to everyone watching the challenge.
Once Duncan rejoins the others after unmasking Chef, he is shown to be greatly concerned when he realizes Gwen is with the real killer.
He joins everyone else in rushing to warn her of the danger.
They become even closer friends in Total Drama Action, which slowly develops into an attraction, despite Gwen denying it at the beginning of the season.
Gwen picks Duncan as her first teammate for the Screaming Gaffers and their friendship causes jealousy to rise from their respective romantic partners, Trent and Courtney, leading to tension to arise in their respective relationships.
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After breaking up with Courtney, Duncan starts a proper relationship with Gwen after sharing their second kiss.
However their relationship is put on hold with Gwen's elimination in Picnic at Hanging Dork, and is strained as Duncan's plan to throw Courtney off her game makes Gwen jealous, as she believes that Duncan still has feelings for Courtney. Alejandro and Heather eventually use Duncan's guilt to get him eliminated.
Even though he isn't close with her at this point, Duncan is angry at Trent for cheating on Gwen by kissing Heather, despite him being framed to look like a cheater.