The office

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Drink Once:

Whenever Dwight makes a beet reference.

Whenever Dwight and Angela have a secret meeting.

Whenever Michael does something socially inept.

Whenever Stanley is shown.

Whenever Michael disses Toby.

Whenever Pam and Jim exchange a longing look (even if it only goes one way).

Whenever Jim plays a prank on Dwight (drain if said prank involves Jello).

Whenever Jim does one of those "idk" looks at the camera.

Whenever Michael puts the moves on a woman.

Any time Jan shows up (drink twice if it's after she gets fired and goes crazy)

Drink Twice:

Whenever any of Michael's girlfriends shows up.

Any time Andy is referred to as "Nard Dog"

Any time Erin is excessively perky

Any time Cecilia Halpert is mentioned/shown

Any time Kelly is shown relentlessly harassing Ryan

Any time there is an interesting conversation at the vending machine

Any time Michael references gender, sexuality, race, etc.

Michael mentions Jan's fake boobs

Drain:

If Dwight tries to one up Michael (even if he's successful)

Dwight's cousin Moze is shown

If Steve Carell wrote the ep

Creed is shown

Phyllis reveals something embarrassing about Michael in high school