For those of you who wear wired headphones, I have done some critical research for you.

They are more strongly attached to the computer, than the friction of the cup and will thusly toss your entire water cup onto the bed, on your cables which will cause it to bounce and fling water onto the nightstand. While this happens my mother will scream from the grave, "This is why you shouldn't set a water cup so close." Which...I mean, yeah. I get it mom.