“Some people will go into debt to give money to someone else, and that’s a huge financial mistake,” says personal finance advisor Lynette Khalfani-Cox. “You have to set firm boundaries and determine the type of help you will give and under what circumstances.” Yes, this includes siblings, children, and aging parents—all people with whom it may be especially hard (but all the more important) to set those boundaries. So, how do you stop family members from asking for money? These tips and steps can help. Are you being asked to help with money in a horrible, unprecedented situation? Or is it to protect someone from the natural consequences of their actions—to enable their destructive behavior? In the latter case, “if the banks won’t lend them money, why should you?” Khalfani-Cox asks. If you’re uncomfortable turning someone down, ask yourself why you feel pressured to say “yes” when your boundaries feel threatened. “You can’t think you are someone else’s financial savior,” Khalfani-Cox adds. “Or that the worst-case scenario will happen if you don’t step in.” If you’re concerned saying “no” will impact your relationship negatively, say so. “It can literally be ‘I don’t believe this is healthy for you or our relationship. I’m not trying to hurt you, but I do need to establish financial boundaries,’” Khalfani-Cox says. Christine Manley, a licensed clinical psychologist based in Nashville, recommends writing yourself a script or role-playing with a partner or friend to help you feel more comfortable initiating the conversation. Manley stresses that setting boundaries tends not to be a one-time conversation: “People think boundary-setting is going to be this really big, tense, awkward conversation, like an intervention.” But in practice, “it’s just saying ’no’ to requests that make you uncomfortable right when the request happens,” Manley adds. A parent of an adult child asking for financial support could say something like, “I want to work toward a place where you’re not dependent on me,” Manley advises. You could add, “I’m still your parent and feel this is in your best interest to help you become a healthier person,” Manley says. Or, you could work with your child to chart a path toward financial independence over a defined period. “Women have been very much socialized to experience guilt when they say ’no,’” Manley says. “Just because that guilt is there does not mean you’re doing something unkind. You’re allowed to say ’no’ to things that make you uncomfortable.” And while guilt may be a difficult momentary feeling, a slow-growing, constantly grating chronic resentment at having given beyond your means can be worse. “Anytime you’re trying to set healthy boundaries, it upsets people,” Manley says. And while people tend to worry most about the people they could offend, Khalfani-Cox says they should worry more about giving in to a request that makes them squirm. “No person’s love and acceptance and close ties to their family members should have to be dependent upon the person’s ability or willingness to provide financial support to the other party,” Khalfani-Cox concludes.