Simon is 13 or nearly 13. He goes to Walter Reed Jr. High in Glen Oak. The new middle child he feels he now has Lucy's bad luck but before that he always was regarded as the lucky one. He has a girlfriend Dina who had cancer and is in remission. He has a dog named Happy. He is good with money and ends up lending it out to his siblings, especially Matt. He has his own room but used to share with Ruthie and before that he shared with Matt. This year he's hit puberty.