Original Commentary
After a while, it's not about the prize itself any more. It's about not wanting to lose and wanting to do something nice for the person you love and trying to make sure the night ends well.

It's 50 cents a try, so he's up to $30. But at this point, it's not about the brant toy. It's not about impressing his woman. It's him versus the machine, and he's not going to back down first - Terrence

Modern Commentary
Yeah, re-reading this, I don't think Jane really wanted the brant toy. She would've been just as happy if he had skipped this. He's fixating on what he wants to do for her rather than what she wants.

Much like Patrick two chapters ago, Robert is tired and could've been charming but isn't. - Terrence