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Dicey first runs into these guys when she's weeping on a park bench in the middle of New Haven, Connecticut. Windy, who's a student at Yale University, offers her a place to sleep for the night and some food. Since the kids are pretty desperate (no food, no money, no place to sleep), you'd think Dicey would jump at the offer, but instead she's pretty leery:
"I'll tell you what I think. I think you don't have a place to sleep, you're probably hungry, you're frightened and worried, and you don't want to tell me anything. So far, am I right?"
He shifted on the bench and turned to face Dicey. "Okay. Now. You don't have to believe this, but you can trust me. I've been in your kind of jam myself, more than once." (1.7.59-61)
Windy and his roommate, Stewart, feed the kids and let them stay for the night, and the next morning, Stewart even offers to drive them to Aunt Cilla's house. Yay. Of course, things go kind of awry when James steals some money out of Stewart's wallet, but luckily, the two boys are willing to turn the other cheek and still help out the Tillermans. Whew.
So basically, Windy and Stewart are the first people that Dicey decides to trust. She spends the beginning of their trip freaking out and dodging adults, but she opens up to Windy and Stewart and accepts their help. This is the moment when Dicey realizes that she's not going to be able to do this all on her own. She needs other people and she can't deny it.
But, even though they give the Tillerman kids a whole bunch of help, Windy and Stewart don't really seem to care about them after they say good-bye. Check it out:
They could never go back to New Haven. She wished they could have stayed there longer. She wished she knew something more about those two young men. She didn't even know their last names. Or phone numbers. Or address. Stewart hadn't even stayed to find out if the Tillermans would be all right. The Tillermans had just drifted through his life, touch in, touch out, and gone without a thought. (1.9.107)
Dicey has told them how iffy their chances are at Aunt Cilla's house and neither Windy nor Stewart ever try to get back in touch with them. They never give them a phone number to call if the kids need it, either. Sure, they were willing to help for the night, but that's the limit to their generosity. But still, they're pretty decent dudes.