Dupree is first seen in Petalburg where he tries to form a romantic relationship with Goombella but fails. Dupree is seen again in Boggly Woods where he tries to warn them about the arrival of the Shadow Sirens. Goombella has the odd feeling of being followed around by him but Mario just tries to calm her down. Dupree appears yet again in Twilight Town where he is turned into a pig like the other Twilighters. The shopkeeper thinks that pig is her husband but when Dupree is turned back into himself, an uproar is caused where he is accused of flirting with the shopkeeper. Dupree is seen again at the hotel of Poshley Heights before the Garnet Star is taken. Dupree then tries to flirt with the Bob-omb ower of the Inn at Fahr Outpost but ends up getting thrown out. Finally, Dupree is seen at the dock on Keelhaul Key where he remains there for the duration of the game.
- Dupree is one of few characters in the game to be turned into a pig and not being a Twilighter. The other being The Traveling Sisters Three.