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personally, I generally use the rough formula: X = desire to do thing Y = foreseeable/predictable/etc negatives Does the activity rate a "still worth it" when considering x -y, if so, do it and to hell with the rest. If not don't. If it hits a grey area wait, and if you want to do it, at some point you'll probably find yourself drunk enough to do it
But I tend to be a little "to hell with other people (we all get hurt sometimes)" about life in general - I would never not do something I wanted simply because it hurts someone else / while on the other hand I consider "potential for drama (that I have to deal with)" a huge deterrent