|My Best Friend's Boyfriend|
|Season 2, Episode 7|
|Air Date||May 18, 2007|
|Guest cast|| Sterling Knight|
Jorge Luis Abreu
|Previous||You Gotta Not Fight for Your Right to Party|
|Next|| Take This Job and Love It|
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.
- The 'Movie Jammies' that Miley wears in this episode are the same ones Lilly wears in You Are So Sue-able to Me.
- Derek Hanson (Austin Butler), Lucas' cousin, had previously appeared as Becca Weller's ex-boyfriend in Oops! I Meddled Again, which explains why Oliver is so amused by Miley's story of the "Worst Date of her Life."
- Larry David and his daughters guest starred as themselves--his daughters are Hannah Montana fans.
- Robby says that all they have on TV are those "stupid dance shows" referencing Billy Ray Cyrus' participation in Dancing With The Stars.
- When Larry David's daughter says: "Maybe Uncle Jerry could get us in," she is referencing Jerry Seinfeld.
- Lilly, as Lola, says "You're despicable" to Miley, as Hannah, in the restaurant. This is Daffy Duck's catchphrase & Lilly/Lola uses a Daffy Duck-accent while saying it.
- Jackson: Rico, why are you doing this? I mean you spent a fortune on this security system, because of a $7 pair of sunglaases and all it's done is kill your business and freezer-burn my butt!
- Lilly (on the phone with Lucas): You hang up first. No, you! No, you! Oh, I'm getting another call. (switches lines) Hello?
- Miley: Hang up already!
- Miley (to Oliver): This is a big moment for Lilly and if you had a romantic bone in your body you able to see that!
- Oliver: Hey, I have eyes. Okay, look. (Lucas says something to Lilly and she laughs) He just said something funny, she laughed. Big whoop!
- Miley: She's not laughing cause he's funny. She's laughing cause he's cute! Boy brains, you might as well scoop em out and store nuts up there.
- Lucas: You are so cute.
- Lilly: You're cuter.
- Lucas: No, you're cuter!
- Lilly: No, you're cuter.
- Miley: Yeah, you're both adorable. Can you pass the salt?
- Romy David: Face it, Dad. She's bigger than you.
- Cazzie David: I bet Uncle Jerry can get us in. (Larry's in shock)
- Larry David: Uncle Jerry?. Why couldn't you say it was your Birthday?. Come on!.