Season 10: Episode 4 - You Do Know What The Lollipop Is For

You Do Know What The Lollipop Is For: When Walden’s old family friend Missi (Miley Cyrus) comes to visit, he now finds her attractive at 19 but is horrified when she suggests he date her mom and starts feeling paranoid about getting old. Jake and Missi meet and fall for one another, but she ends their short-lived fling when she leaves to get back together with her boyfriend back home. Walden and Alan console Jake and the three of them bond over their relationship woes.