Bender just does not care that Claire it's a princess, he constantly gets her out of her system.
Here are some quotes:
Bender: Claire, you wanna see a picture of a guy with elephantitis of the nuts? It's pretty tasty.
Claire: No thank you.
Bender: How does he ride a bike?
Bender: Oh Claire, would you ever consider dating a guy who looked like this?
Claire: Can't you just leave me alone?
Bender: I mean even if he had a nice personality and a cool car... although you'd probably have to ride in the backseat because his nuts would ride shotgun
John Bender: [after Claire flips him off] Oh, obscene finger gestures from such a pristine girl.
Bender: Being bad feels pretty good, huh?
John Bender: [after Claire performs her lipstick trick]
[Claps sarcastically]
John Bender: Wow, Claire. That was great. My image of you is totally blown.
Allison Reynolds: You're a shit. Don't do that to her, you swore to God you wouldn't laugh.
John Bender: Am I laughing?
Andrew Clark: [shouts angrily] You fuckin' prick!
John Bender: What do you care what I think anyway? I don't even count... Right? I could disappear forever and it wouldn't make any difference. I might as well not even exist at this school, remember?
[Turns to Claire]
John Bender: And you... don't like me anyway.
Claire Standish: [pause] Did you really think what I did with my lipstick was gross?
Bender: Honestly?
Claire Standish: Yeah.
Bender: [nods] No.