Bill does kinda come across as a bit of a masochist at times indeed!
Does anyone remember Marvin the depressed robot from Hitchhikers ?
Marvin: I've been talking to the ship's computer.
Marvin: It hates me.
Marvin: I think you ought to know I'm feeling very depressed.
Trillian: Well, we have something that may take your mind off it.
Marvin: It won't work, I have an exceptionally large mind.
Trillian: Yeah, we know.
Marvin: Life? Don't talk to me about life!
Trillian: Marvin... you saved our lives!
Marvin: I know. Wretched, isn't it?
Marvin: I've calculated your chance of survival, but I don't think you'll like it.
[Marvin, Trillian, Ford, Arthur and Zaphod are being fired upon by Vogons - the others flee as Marvin only very slowly walks away]
Marvin: I don't know what you're all worried about. Vogons are the worst marksmen in the galaxy.
[he is shot in the back of the head]
Marvin: Now I've got a headache.