Two things:
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Generally when you take medicine with high acidity food, like coffee, it will break down your medicine prematurely - you won't get as strong as an effect. I had to stop taking my Vyvanse with orange juice because it basically nullified the medicine.
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Talk to your doctor. I had chronic headaches that I found out were related to low blood pressure and dehydration. Drinking water instead of diuretics, like coffee, immensely helped me.
If you've ever looked into email protocols you'd find it's a nightmare of cludged together solutions piled on-top of each other over decades. It simply isn't designed for instant messaging.
Here's a great talk that goes into a bunch of issues with email in general.