Mainly your food seems extremely high. If you don't mind the tasty Lipton noodles ($1), Shells and Cheese ($1.50), Frozen Pizza ($2), Hot pockets ($3 for 2), Spaghetti (~$2), Canned soup ($1-2), Cereal ($0.25)... you can eat a lot of cheap meals. I don't see why it should be hard for someone to eat nicely at $300/mo.

For instance, last night I ate a chicken breast ($1), mashed potatoes (instant kind - $2), and green beans (can - $1.50), with a can of Coke ($0.25)... a decent meal for $4.75.