Would you consider dating this guy?

Girl absolutely not. First of all fuck a high school fling the last thing you need to do after a divorce is get in a worse situation than you were before, also think of your child! I would absolutely never date someone like that knowingly and put my child in harms way. Men always have a story when they have crazy shit on their record and I’m 100% sure he’s lying on why he did it. Red flags everywhere he sounds crazy.