Drink 10floz(1 bottle) of Vicks NyQuil or 2 bottles for nightmare difficulty, and then quickly try to masterbate before you fall asleep. If you succeed you win!
I got about 20seconds into the NyQuil challenge on nightmare mode before losing, but I was already tired when I started.
On a boring night, you take 2 doses of Nyquil while at least one other buddy waits for you to sleep for at least 1 hour. Make sure to pick out a spot at least 10 feet from your bed. Your friend wakes you up and screams nyquil challenge as loud and as fast as he/she can and you run towards the spot you picked out and try to make it back to your bed and back without falling or passing out.
Bud - "DUDE!!! WAKE UP!! AGGGHHH!! NYQUIL CHALLENGE!!
You - "HUH!?! What??"
Bud - "NYQUIL!! NYQUIL!! RUN RUN RUN!!
You - "Oh S&^@! ughhh"