Take a drink when:

Adrian Monk says Wipe

Sharona says/threatens/ mentions she’s going to quit.

Natalie is very enthused and/or trying to get Monk to do something or trying to encourage him or trying to make him feel better

Julie gives a concerned or worried or unsure look when Monk is acting strange or doing his stuff he does when he’s trying to solve the case.

Leland gets all stressed or loses it

Disher messes up or says he really blew it this time lik this time takes the cake.

Special:

Finish your drink when Adrian Monk explains what happened

Decide your future drinks when Mohk is doing that thing with his arms and hands as he’s examining the crime scene.

Ask yourself if you are becoming an alcoholic/drinakaholic or not when Adrian Monk says here's the thing. If some claims you are but you don't think you are, when he says that line you state your case on this.

Try a new drink when Monk is trying to overcome a fear or phobia.