"I play to detriment" is a set of words that always worries me when I hear them from a new player - or even from more established players. It is a phrase that can be very good, but that can also be very bad. Often times people don't realize that both definitions exist, and that they are not mutually exclusive. Today I want to talk about "playing to detriment" and how you can do it as a good thing, but also how you can do it as a bad thing.
Doing It Well
Playing to Detriment well often means making things worse for yourself. This means walking into ambushes that impact your character, letting bad guys go who will hold a grudge against you, or otherwise taking actions that are not ideal or otherwise are harmful, but where the brunt of the consequences will fall on you.
D'artagnan throwing Rochefort a sword so they can fight as equals to get his satisfaction is the "good" type of playing to detriment. Sure, now D'artagnan has a hard fight and Rochefort has a sword, but that is a problem for him to take.
The lovestruck barbarian trusting the charming spy - even as everyone at the table knows it is a trap - and going along with them to the inevitable kidnapping and ransoming is the good kind.
Generally speaking if it makes things worse for you, or primarily for you, it's the good and fun type of playing it.
Doing It Poorly
On the otherhand, if the chief victim of the consequences is other people you are probably doing it poorly. By this I don't mean no one but you should suffer from your action, but the second it hits the other players in a negative way you're probably doing something wrong. In otherwords, as my housemate says "your right to flail about with your fists ends at my nose." It's cool to throw random punches, but if you hit someone - that's on you.
Consent Is A Wonderful Thing
The catch to the "if it impacts you it's fine, if it impacts me it's bad" is if I - or whomever is going to also get caught in the problem - gives consent for this. Consent can come in a number of ways. We can talk about what you're planning, how it could play out, and how it could work out in the end. We can pre-discuss consequences and what that can mean. We can discuss the whole thing. Alternatively, you can just ask if something is ok in the moment and I can nod and say 'do it.'
Generally, consent is a wonderful thing to have whenever you're doing some weird interactions with other players, or ones that can cause drama. For example, in a Star Wars game I'm in, my character has a tendency of taking pictures (not creepy ones) of one of the party members. I've discussed this with the player, and we've agreed to it. Now when it happens, and when it causes drama, we know we're both on board.
Simple But Effective
Playing to detriment is nuanced enough I could talk about it and specific examples for years and still not hit a consensus. Ultimately, you know your group and fellow players. You know your GM. You also know what kind of game everyone is going for. Try to keep your detrimental actions so they only hit you, or talk to your fellow players, but in the end what is and isn't acceptable is going to change from table to table.
Just try to keep the game fun, for everyone, and you should be fine.