Anyone who has been in the cycle of giving a family member money knows precisely how it goes. They mess up, you fix their problem by throwing the money they ask for at it, and they keep making the same mistakes over and over again because they know that they have you to fall back on. It obviously depends on the person, but once you tell someone through their actions that you will bail them out whenever they’re in a bind, they will be more likely to rely on that service. Despite what some prideful people say, it’s extremely easy to ask someone for a couple of thousand bucks, especially compared to the effort it takes to save a couple of thousand bucks. Whether it’s easier to set boundaries with a family member about borrowing money or cough up money that barely makes a dent in your savings is the real question.