I am unsure if I am remembering two books mushed together or one book in total but this is what I have so far.
Illustrated, somewhat dark-covered middle-grade novel available in a U.S. school library around 2015. A boy lives with his father or grandfather, who has exhausted the family’s savings publishing a memoir or novel that fails to sell. Facing the loss of their home, the boy enters a Millionaire-style television quiz show. A magical voice in his head converses with him and supplies answers. Earlier, the boy and a girl get jobs together at a bakery. They eat enchanted bread that makes each eater fall in love with the first person they see. The girl’s mother previously ate the same bread, fell for a stranger, and abandoned the family.

Any help would be appreciated. I know for certain it is not Just Add Magic or Jenny’s Ear.