At least this way, Anakin is consenting to being the object of bets in a sporting event. And excited about it. He hasn't really thought about how to provide for them (yet) but if he has this kind of option, he'll take it. It's fun, at least for him.

He hasn't (yet) thought of how his presence will (more) complicate Obi-Wan's life (again).

But he feels the arm tightening around him and just leans into it a little. Alone - or not pretending they don't know each other well - Anakin would have leaned his head on Obi-Wan's shoulder and enjoyed the attention, rather than running the course at all. More than anything else - even the idea of money and using it on food to eat - is the idea that Obi-Wan might believe Anakin was pushing things too far, so instead, he nods. "I'm ready, I think."

He knew, but kept his voice seeking for approval.