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Something worth noting I think is that Jesse and Dickie are both the first people around Matt’s age and I think the first non family members who don’t comment on his weight. The fact that they keep him on “their level” really solidifies them as being his peers. As @caseybold mentioned Matt is attracted to Jesse from the first moment that they meet; this can affect even a well-intended friendship.

“What makes us feel more than ordinary sympathy for them?”

I believe that the emphasis the author puts on the social and economic standings of Jesse and Dickie do a lot to cement them as needing positive attention and support. Matt sticks up for them to his grandmother who immediately refers to them as being “lesser than.” His conscience leads to him paying for the things they “stole” from a convenience store, which affects Jesse and Dickie to such a degree that they vow to not shoplift anymore. Not only are these children looked down upon by townsfolk but their entire families are scorned and shunned.

While some of these reactions are a little over the top in my opinion (mayyyybe the church picnic), it certainly isn’t outside of the realm of possibility and unfortunately has happened many times in the real world. When we as the readers witness a couple of 12-14 year old children being cussed out and socially stepped on, it gives us a real reason to want to see these kids pull through and become stronger through it.