Basically, when Pony sees Bob's picture in the yearbook, he just starts to wonder about Bob as a person. He had never really thought of what Bob was like -- he had just seen him as a sterotypical Soc who was always a jerk (or worse) to the Greaser types.
But now he starts to wonder about Bob. He wonders about the Bob that Cherry Valance knew. He wondered about whether Bob had a brother. He wondered how it was that Bob was (according to Randy) the best friend a person ever had.
He wonders a lot of things like that, but the overall idea is that now he is seeing Bob as a real person.
For more details, look this up in the book -- it's right at the start of Chapter 11.
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