Tyler goes on a dog-walking date with a girl he likes, Nikki, and her dog.
- G. Hannelius as Avery Jennings
- Blake Michael as Tyler James
- Francesca Capaldi as Chloe James
- Stephen Full as the voice of Stan
- Regan Burns as Bennett James
- Beth Littleford as Ellen Jennings
- Mick and Kuma as Stan
- The title of the episode, Wingstan, is a pun on the word wingman.
- This episode aired right after the Disney Channel Family Night Special Event Sofia the First: Once Upon a Princess.
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