|Killing Me Softly With His Height|
|Season 3, Episode 5|
|Air Date||14th December 2008|
|Previous||You Never Give Me My Money|
|Next|| Would I Lie to You, Lilly?|
Killing Me Softly With His Height is where Miley meets a guy named Conner while Christmas shopping. She accepts his offer to go on a date with him, but he's shorter than herself.
Miley and Lilly go Christmas shopping in the mall. When they see a cute guy sitting behind a table Miley calls dibs on him. During their talk a girl named Sophie shows up and asks if Oliver would go out with her. His refusal with the reason of her having to small feet results in Miley saying that she doesn't understand how someone can turn someone else down because of a physical thing. Connor agrees and asks Miley to go to the holiday carnival with him. She agrees. Then Connor stands up and it turns out that he is a lot smaller than Miley. After Connor leaves the room, Miley is angry because she doesn't want to go out with someone smaller than her, similar to Oliver. So Oliver blames Miley to be exactly like him, just that she isn't willing to admit it. Miley disagrees.
At the same time Robby tries to fix the Christmas tree because it doesn't stand straight. It results in a tree which is "straight as an arrow" but very short. Jackson comes in and notices this and Robby defends himself by throwing the tree away and saying he just made firewood. Jackson continues and says that he comes back from the College of Santa Barbara. Robby finds out that Jackson didn't look at the college itself but more at the girls. Since Jackson doesn't have that good grades he figures out that he needs a letter of recommendation, which he can get from the Stewarts' neighbor, Mr. Dontzig. To get the letter Jackson has to impress Mr. Dontzig by doing him good things. This includes gloving his head, cleaning his feet, clipping his toenails and laughing at his Jokes.
At the holiday carnival Miley and Connor are talking. Also Miley wins a little Hannah Montana figure and Connor wins a stuff bunny which is bigger than himself. Suddenly a mum interrupts and asks Connor to ride on a train with her son since she is too big and her son is afraid. Connor agrees and leaves with the kid. Meanwhile Oliver and Lilly can talk to Miley, making fun at her because she is taller than her date. She claims that they are having a great time. When Connor takes Miley home he tries to kiss her but she doesn't want to. She makes up an excuse but he finds out that she doesn't want to kiss him because he is smaller than him. Still she notices that he has brown eyes and that she likes people with brown eyes but she doesn't like Connor because of his size. He says that Miley is just like everybody else and leaves. At the next day with Lilly at breakfast she accuses Miley dumping Connor just because of his size. She eventually realizes that Lilly is right and now imagines what would happen to Hannah Montana if she was small. In her imagination Hannah gets disliked by everyone. Because of her guilt she decides to apologize to Connor.
Meanwhile Jackson and Robby have to do Mr Dontzig's laundry to get the letter of recommendation. Dontzig brings the letter but wants Mr. Stewart to do something before Jackson gets the letter. His sister is a big Robby Ray fan, so Robby should meet her. Robby agrees with the hope that she is nice and pretty. It turns out to be wrong, she is as fat as her brother, Mr Dontzig. At first Robby mistakes her for Dontzig with a wig.
In the mall Miley tries to apologize to Connor but she can't because he is working as an elf. Eventually she and Lilly have the idea to dress up like a reindeer to be allowed to talk to him.
Jackson finally gets his letter of recommendation, but he rips it because he says that it wasn't worth it that Robby had to go out with Mr. Dontzig's sister.
Back at the mall Miley can finally talk to Connor but he first doesn't want to take Miley's excuse. Eventually he gives her a second chance because Miley admits that she was wrong . She also says that she loves his brown eyes.
Dontzig wants to give Jackson another chance, but Robby doesn't want to go to Dontzig's really good looking cousin.
For a Christmas present Jackson afterwards gives both Miley and Lilly one of Miley's clothes.
- The episode's name is based on the song "Killing Me Softly with His Song".
- This episode marks the final appearance of Mr. Dontzig.