"My Best Friend's Boyfriend" is the seventh episode of the second season of the Disney Channel series Hannah Montana and the thirty-third episode of the overall. It aired on May 18, 2007. It was written by Jay J. Demopoulos and directed by Roger S. Christiansen. The episode's title refers to the song "My Best Friend's Girl" by The Cars.
Lilly is dating a boy named Lucas and at first, Miley couldn't be happier for her. But then she eventually feels like a third wheel, and gets sick of the two of them being together. After telling Lilly of her displeasure, Lilly decides to have a sleepover with Miley, but Lucas is invited as well. But Lilly makes up for it by setting Miley up with Lucas' good-looking cousin Derrick Hanson. Miley is at first excited, but while they're all watching a horror movie, Derrick gets freaked out really easily, much to Miley's annoyance. After he eventually jumps on her lap, Miley calls it the worst date of her life. The next day, Miley sees Lucas kissing another girl. Miley later confronts Lilly with the news, but Lilly doesn't believe, thinking that Miley's just jealous. Miley tries to prove to Lilly that her new boyfriend is cheating on her and flirts with Lucas so that he'll cheat on Lilly with her.
When that doesn't work, she dresses up as Hannah Montana and attends a restaurant with Lilly (as Lola in one of the most memorable outfits). Lucas and Oliver are at the same restaurant and Hannah flirts with Lucas from across the room. When Lola notices this, she is infuriated. Lucas eventually comes to give Hannah his number, but Hannah is interrupted by an adoring fan and her controlling grandmother. Hannah leaves the table to take a picture with the fan and leaves Lola with Lucas. Lucas tells Lola that he has two girlfriends and would dump them both for Hannah Montana. Realizing her best friend was telling the truth, Lola gets mad and angrily dumps shrimp sauce on him. When Hannah returns and congratulates Lola, the latter smugly replies, "Wait till Lilly gets a hold of him." At the end, Miley and Lilly make up and decide that the next time either of them has a boyfriend, they should trust each other no matter what. Then, the controlling grandmother comes over once again, mistaking Oliver for Natalie Portman (claiming "You look cuter on TV").
In a subplot, Rico believes his store, Rico's, has been robbed and installs an expensive security system that confuses Jackson and traps him various times. When Jackson finally decides to quit because Rico asks him to sign a liability waiver, he and Rico realize that their "robber" was actually just a raccoon.
