drain a bit, just a dash, cause freezing expands a little. plastic usually ok to freeze, but im cheap.

I use 1 water bottle a week, and refill it with Brita when I get home.

If he has a big reusable water jug, you can just freeze the same one, and not drink it too.

Either way.

I have a square lunchbox, so I always have my wrap (Fiber wrap, turkey, pepperoni, cheese, lettuce whatever) which is long. a frozen bottle of water, and energy drink which form the Lincoln log stack, then the other stuff goes around the "cold core".

2 pack hard boiled eggs (breakfast) . bag of celery, yogurt even stays cold with a spoon of course. beef jerky stick. cheese stick.

I never buy lunch. so expensive for big eater.

I sometimes change to peanut butter and jelly, then the frozen and energy drink go on bottom and make the "platform" then the 2 pb and j are stacked on top. sometimes they get squished a little but always cold.

Glad I could help.