If I drink 1 cup of milk each day..,?!

Eat as much as you can at night, things like milkshakes and peanut butter and meat..

Try to eat while your not doing anything, so basically you want to eat just before you go to bed (but brush your teeth after!!)

Well it depends on why you want to gain weight. If your young I really wouldn't worry about it, because as you get older you will gain weight eventually. But if you really want to gain weight because of medical reasons, I agree with eating at night because you will definitely gain if you sleep on what you eat before bed. And yes you should brush your teeth afterward cause we don't want cavities!

Eat fattening foods....gravy/mashed potatoes, fried Chicken, then just before bed, have brownies w/milk, cake, pie anything fattening w/milk....then go to bed. Don't give it a chance to be worked off. You'll be fat in no time.
Yes, drink whole milk during the day w/cookies.

The doctor prescribed whole milk with ice cream to my friend to help her gain during pregnancy. I think it was a cup of milk and icecream mixed together twice a day.

Anything in high protien. Milk, mixed with protein shake powder will help. but before using protein shakes, talk to a doctor

I wish I was you.
Just eat when you want, what you want, whenever you want.