Season synopsis
Contains spoilers for this season and earlier seasons.
Miley’s friends begin growing up alongside her. Lilly and Oliver become a couple, which leaves Miley trying to support them without turning every disagreement into a crisis. Oliver’s health also becomes a serious part of their friendship when Miley and Lilly learn that he has diabetes. Miley’s own dating life shifts when Jake returns and she secretly gets back together with him; she worries Robby will disapprove, so she pretends to be interested in bandmate Jesse instead. That ruse becomes harder once she develops real feelings for Jesse.
In the two-part “He Could Be the One,” Robby helps Miley sort through those feelings rather than choose for her. Miley turns down Jesse and picks Jake, explaining that their connection is special, and Robby accepts the relationship after checking that she is sure. Later, Lilly’s mother takes a job in Atlanta, and Lilly briefly moves in with the Stewarts. The arrangement strains the girls’ friendship, but Lilly decides to return to her father before Miley talks her into coming back.
The season ends with a larger change at home. Miley misses Tennessee and asks Robby to bring her horse Blue Jeans to California; when Blue Jeans keeps escaping his stable, she wonders whether she should move back. Robby understands that she wants the feeling of home, not necessarily to leave her friends, and reveals a ranch near the Malibu beach. The family moves there, and he cancels Jackson’s apartment lease so Jackson can join them. The friends leave the old house together, although Oliver is preparing to go on tour with a band. Miley can stay near Lilly while finding a home that gives Blue Jeans room too.