It goes without saying: drink responsibly! With that out of the way...

Take a sip when:

You laugh out loud at someone's joke
Someone makes a joke relating to penises, dildos, or masturbation
Someone uses something which only exists in the real world to explain something in the game world
- Take a second sip if Griffin creates an in-universe justification for this (e.g. Craigslist is a literal list made by a gnome named Craig)
Someone makes a joke involving a nonexistent check (e.g. a “zestiness check”)
Travis/Magnus begins a sentence with “I rush in and”
Taako casts Magic Missile
Taako’s cooking, cooking show, or quest to create the taco is mentioned
Merle casts Zone of Truth
Clint/Merle uses or references the Extreme Teen Bible
Clint/Merle references Pan
A monster or enemy explodes, is fully or partially bisected, collapses into uncountably many pieces, or otherwise faces the receiving end of a Curb-Stomp Battle at the hands of the party
The party’s blatant stupidity/recklessness is mentioned
Anyone rolls a natural 20
Griffin forgets how one of his characters is supposed to sound
Griffin does a character voice silly enough to get a laugh out of someone in the party

Take two sips when:

You laugh out loud at something that was only unintentionally funny
Someone tells a joke involving a character’s name
Someone mentions that Travis and Magnus have become indistinguishable
Taako steals something
Merle casts Zone of Truth without the spell succeeding
Merle or Taako casts Charm Person
Anyone rolls a critical miss
Griffin unexpectedly makes someone in the party roll a constitution or dexterity saving throw
- Take a gulp if he makes the entire party do this
Any of the three players complain about character voices
Clint tells a joke that makes Griffin uncomfortable
LGBT themes are explored
The players refer to their roommate as “Pringles”
The party does something rude to Angus
The party does something almost certainly lethal under the justification that they'll be revived anyway.
Killian does something very aggressive
Davenport says his own name
Julia is mentioned
Upon a second, third, etc. listen to an episode, you notice Griffin foreshadowing something
- Take a gulp if it's something big. Finish your drink if it's something big and you're kicking yourself for not noticing it the first time you listened.

An episode ends on a cliffhanger
- Finish your drink if it ends with at least one party member literally hanging off of something
A major character dies
Someone laughs for more than five consecutive seconds (enough to disrupt the flow of the podcast)
A player does something which makes an intended challenge much easier than it otherwise would have been. Take a second gulp if this player is Justin.
A Grand Relic directly results in multiple people’s deaths
Red robes make any appearance. NOTE: DOES NOT APPLY DURING THE STOLEN CENTURY
Someone’s name is a portmanteau of two common names (e.g. Craigory)
Magnus tears or cuts someone or something’s arm off
Magnus suggests slapping another character
Merle actually heals someone
Any party member goes below 0 HP
Griffin begins a sentence "I'm talking about [plural noun] like" when explaining either a sponsor or something related to the Maximum Fun Network
Justin bears witness to Clint doing something silly
The Adventure Zone fan community is explicitly mentioned
You get the Fantasy Costco theme song stuck in your head

A Grand Relic is destroyed
Taako first uses the line “ABRAKA – FUCK YOU!”
Klarg makes an unexpected appearance in Goldcliff during the Petals to the Metal arc
- Finish two drinks when this happens in the Live Boston Stunt Spectacular
Justin/Taako monologues about choosing the mongoose mask
Garyl is summoned
Merle loses his arm
Magnus sees himself as a Red Robe

Take two sips of water whenever someone mentions children watching the podcast.
Almost take a sip, then reel away in disgust, whenever someone mentions inoculation.
Classily take a gulp every time Madame Director swears.
Take a gulp for every second you spend laughing after Taako trades the Slicer of T'pire Weir Isles for the Flaming Poisoning Raging Sword of Doom.
Mournfully take a sip every time someone fails to resist the thrall of a Grand Relic.
Set down your drink and contemplate your life choices every time the podcast becomes particularly dark.
Die of alcohol poisoning starting at the 89 minute marker in Lunar Interlude V Reunion Tour Part Two.
Take a double-strength shot and slam the glass in Lunar Interlude V: Reunion Tour Part Two when Lup is revealed as Taako's twin sister.
Cry yourself to sleep when Hurley and Sloane transmute into a tree. Or when Magnus' backstory is discussed in The Eleventh Hour. Or any time a world is consumed during The Stolen Century. Or when the Red Robes sans Lucretia lose their memories. Or whenever you feel like it.
Check yourself into an ER if you finish two episodes while playing this game.