Well of course, in your hypothetical situation, you're at least getting SOME liquid and he is getting NONE.
Perhaps dehydrate isn't the best word to describe the effects of caffeinated drinks. A better way to say it would be that they do not hydrate well AT ALL. Your body may be able to get liquid from the caffeinated beverage, but in the end it won't be much, and I'm not so sure that in the end you'll end up with any really positive result.
Drinking a caffeinated beverage while working out, while it may deliver SOME water to your body, delivers such a small amount overall that you do run the risk of dehydration.
It's quite simple really. Caffeine is a diuretic. You can sugarcoat it all you want and wish to believe that caffeinated drinks can still hydrate well, but it's simply not possible. Caffeinated drinks chemically MAKE your body digest less water and, as such, cannot hydrate you to any significant degree.
Case in point, I drink caffeine all the time and water only every now and then. I barely ever sweat. Why? Because I'm not very hydrated. I'd have a lot more energy if I drank awter instead of caffeinated drinks and I'd be a lot more hydrated as well. It's a simple fact of biology.
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"Musicians are the carriers and communicators of spirit in the most immediate sense." - Kurt Elling
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