@DavidK Yup the right response is to escalate to your managers or HR if your colleague doesn't get it… I guess this less professional solution is a better cultural fit for OP's team…
@David K: Do you even know what "passive-aggressive" is? What I have suggested is "mirroring" (sometimes called "pacing"). - It may be aggressive but it is anything but passive.
@DavidK This isn't passive-aggressive, because when asking the coworker to donate to the nag-jar OP would be doing directly to their face, not hiding behind anything (like note or non-commital language that some people use)
@DavidK: It's mirrorring the behavior in order to let the other guy realize how annoying he's being by making him the recipient of the same type of behavior.
I think this is going to fail because if I would be the other guy, I would participate and put the money to the nag jar and ask you to do the same kind of participation to swear jar. And it won't help your possible image of "not team player"
@SteveJessop then the "nagger" still win because that is what he wanted all along. The issue is not money with jars, it is just a reminder of our actions we are not aware. I think the all issue is unnecessarily overblown by both parts anyways.
@ifyalciner: I guess after a few weeks of that the questioner can suggest a more efficient system, that whenever the nagger feels like it they can put some money straight in the swear jar rather than going via the nag jar. If the nagger would consider that a victory then, OK, I can't stop people putting money in jars if that's what they want to do! At least, not without raising it to some kind of complaint about workplace harrassment, which the questioner would prefer to avoid.
@ifyalciner: No -- Arqan's position is "I'm not playing the swear jar game. At all. Ever. Instead, I am playing the nag jar game. If you nag, you are playing my game." The game is not "25 cents makes your nag successful"!
@ifyalciner: but actually I don't like the nag jar game anyway, because if I didn't want to play the swear jar game then it would be because I also didn't want to play the "making up rules for other people to follow enforced by stupid jars" game. But having committed to the nag jar game, and had my bluff called, I don't think the game ends immediately with a victory for the nagger, I think it continues to play tediously out...
@A.I.Breveleri "of or denoting a type of behaviour or personality characterized by indirect resistance to the demands of others and an avoidance of direct confrontation." You're using a silly little game that's similar in nature to make a point ("see how annoying this is") rather than just having a direct conversation with the person. That's definitely passive aggressive. It may also be "mirroring", but that's beside the point.
@AnthonyGrist: This seems a bit like saying boxers are passive-aggressive, because punching somebody back is not direct resistance to the punch they just landed on you, it's indirect ;-) One has to decide whether "I decline to pay your fine, and furthermore I am escalating by claiming that you owe me a fine" is a direct or an indirect resistance, and whether choosing to enter that conversation constitutes "avoiding direct confrontation". Note also that the direct conversation has already happened multiple times, so this is not "rather than just having a direct conversation".
@AnthonyGrist Direct confrontation has already proved to fail. The options left over are (1) to accept defeat, (2) to put up with the nagging, (3) to escalate which in this context means the involvement of an authority, or (4) to try a different approach without escalation. Considering the undesirability of 1 and 2 and the dangers of 3, 4 sounds like a very sensible approach. It is confrontational but not direct, although it's far from underhanded.