|Family & Friends|
|Family:|| Miley Stewart (Future Sister-in-law)|
Siena is Jackson's current girlfriend and future wife. She is a bikini model, and is extremely rich. Jackson met her at the beginning of Season 4, and grew very close to her. She learned Miley's secret before it was publicly revealed, and remained with Jackson though he wasn't rich or famous.
Episodes: Sweet Home Hannah Montana, Hannah Montana to the Principal's Office, California Screamin, De-Do-Do-Do, Da-Don't-Don't, Don't, Tell My Secret, Love That Lets Go, I'll Always Remember You, I Am Mamaw, Hear Me Roar!, Wherever I Go
Jackson meets through her rude cousin who happens to be the Stewart's neighbour in the season four premier episode, Sweet Home Hannah Montana. Siena is Jackson's unofficial girlfriend, though the romantic feelings are mutual. Siena is Jackson's longest running girlfriend. As of California Screamin they have been together for three weeks and have kissed each other. Rico is shocked by the relationship, wondering how a girl as hot as Siena could ever be with a guy like Jackson. He was so shocked when they kissed, that he fell out of a tree. Due to Siena being away doing a photo shoot in Peru, Jackson was away from her for a week and decided to help Rico out in returns for a $2,000 check which he spent on a ticket to Peru.