Drink whenever both the Caretaker and the Town Crier take up two slots in the same stress relief areas.
Drink whenever a hero goes missing in the Hamlet for the week. Also drink if you return to the Hamlet only to realize a hero you've sent for stress relief is still unavailable.
Take a shot every time you send a hero to the Bar. This also applies if the hero stays in the Bar for another week.
Take another shot if someone comes back with "Tippler", or has the "double vision" or "moving sluggishly" debuffs.
Take a sip if you failed to disarm a trap.
Take a drink if you forgot to disarm a trap.
Take a drink every time a hero's quirk causes them to immediately activate a curio.
Take another drink if the effects of the curio are negative.
Take another drink if you have an Antiquarian in your team and you miss out on their Antiques this way.
Take an extra shot if a Kleptomaniac/Egomaniac hero stole the loot from the curio.
An extra sip if you had a supply item that you could have used on the curio.
Take a shot if it was a Shambler Altar that you planned on using.
Take a shot every time a hero gains a negative quirk or disease from a curio.
Raise a toast if the hero gains a positive quirk or loses a negative one. You can do the same if a positive quirk becomes locked this way or it they lose a locked negative quirk.
Drink in frustration if the hero gained a situational positive quirk that displaced one of their more useful ones.
Take a drink if you encounter an obstacle and you have no Shovels to clear it out.
Take a shot if you received a Hunger check and didn't have enough food.
Chase it down in frustration if it was because you didn't account for the "+% Food Consumed" stat.
Drink in celebration if you find a Very Rare (or better) Trinket from by random chance (Loot from battle, curios, Trinket Scrounge).
Down a glass of wine if you find the Tempting Goblet.
Take a sip if you discover a secret room.
Drink in frustration if you have no keys for the Ancient Artifact.
Take another sip if you earn a Head Trinket from it.
Have a beer when you realize one of the patches nerfed it into a normal chest.
Take a sip if a party member gets moved to a position where they can't use any of their skills.
Take a shot if your party gets shuffled and at least two of your heroes gets shuffled into positions where they can't use their skills.
Take a drink if an enemy lands a critical hit on at least two heroes.
Take a drink when every hero receives a DoT, debuff, or Horror from the same attack.
Take a shot if at least two heroes get stunned by the same attack.
Take a shot when a hero gains an Affliction (once per dungeon).
If you have DLC enabled, add The Fanatic and The Thing from the Stars to that list.
Take a shot if a Shambler randomly spawned in pitch-black light or if you didn't know what the Shambler's Altar is and you randomly tested items until you got a "result."
If the Brigand Pounder misfires, take a moment to collect yourself, then drink.
Take a sip if a hero dodges or resists getting charmed by the Siren.
Take a shot if Wilbur stuns your healer before they could've healed a hero who gets killed by the Swine King.
Take two shots if Wilbur directly kills a hero.
Have a celebratory drink if no one becomes Afflicted at the end of a Shrieker fight.
Take a shot if a hero receives a negative Shrieker quirk.
Take a shot if the Hag or Fanatic kill a hero immediately after they're released from the pot or pyre.
Drink if you obtain an achievement from Yet Another Stupid Death, unless you were actively seeking them.
If a hero gains the Resolution quirk, don't drink for the rest of the dungeon.
If they received it after clearing a dungeon or in the Hamlet, don't drink until you go into a new dungeon.
Take a sip every time a quest gets screwed over by the Random Number God in some other fashion (it doesn't have to be listed on this page). Caution: This might still kill you.
If you're on Stygian or Bloodmoon difficulty, finish your drink if you lose due to the time or death limit.
Take a drink every time someone lands a critical hit. If you like living dangerously, apply this rule for critical heals too. If you value your liver, don't use anything strong.
Take a drink every time someone misses or dodges an attack. Again, don't use anything strong unless you want to put your liver on Death's Door.
DLC:
Take a shot every time a hero gets infected with the Crimson Curse.
Take a sip along with an infected hero in your active party when they chug a vial of the Blood. (If it counted the inactive ones too you would likely die.)
Take a shot in substitute for each missing blood vial in the inventory for your team of "wasting" Crimson Cursed adventurers. Don't drink if that hero is holding the Rat Carcass.
Take a sip every time a hero infected with the Crimson Curse does something to mess with your strategy.
Take a shot if they bring a friendly hero into Death's Door.
Take a shot if a hero interacts with a Wine Crate when you really needed it for Firewood.
Drink if your Flagellant used Exsanguinate and misses.
Raise a toast if your Flagellant miraculously saves the day during the Vvulf invasion. He seems surprisingly well-suited for the event.
Raise a toast if your Flagellant demonstrates to be a One-Man Army, especially while he's Rapturous.
Drink in celebration if you find a Crimson Court set trinket from an unexpected source. (i.e. not from bosses or quest completion)
Drink in celebration if you find and rescue a hero from the Courtyard.
Take a sip every time a you bring a Bloodsucker enemy down to low health but it heals back to full before you can finish it off.
Take a shot in frustration whenever a Gatekeeper retreats before you could kill it for an invitation.
Take a shot every time you are forced to abandon a team member while escaping a full wipe from the Fanatic.
Take a drink if the Shieldbreaker had at least 40 Stress when the nightmares happen.
Take a sip every time a snake inflicts Damage Over Time on the Shieldbreaker.
Take a drink if a snake lands a critical hit and stresses out the Shieldbreaker.
Take a sip whenever you get shuffled by a Plow Horse.
Take a drink when the Sleeper's Herald's Reality Bend debuff or a trinket makes you target an unintended enemy.
Take a shot every time you can't destroy a Crystalline Aberration or one of the Fracture's crystal formations before it blows.
Drink to celebrate whenever a hero gains a Prismatic Quirk.
The Butcher's Circus:
Take a sip if your match is rendered null from a desync. Take another if the desync happens while you had the upper hand.
Take a sip if your opponent surrenders while still having 4 heroes alive.
Take a sip if one of your heroes dies in the first round of actions.