Saying "no" is hard. Saying "no" when a family member is asking for help—and that help comes in the form of money? That can feel impossible. Here's how to set money boundaries and save face.

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Saying "no" to someone asking for help can be a difficult thing for many of us. This can be especially true when the people asking for help are family—and the help they're asking for is money. But as plenty of folks who have done so will tell you, mixing family and money can bring complications, especially when all you really want to say is "no."

"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 with your siblings, your own children, and aging parents—all people with whom it may be especially hard (but all the more important) to set those boundaries. These steps can help.

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Ask yourself key questions.

People lose jobs. They get sick or get into accidents, they have messy divorces, and they hit rough patches in life. The question to ask is whether the situation causing a person to request help from you is a rare crisis—or the reflection of long-term financial drama. 

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 own 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." 

Prepare these answers instead.

When turning down a request for financial assistance, you don't need to justify your actions or provide any explanations. A simple "no" can suffice. 

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. 

She stresses that setting boundaries tends not be a one-time major conversation. "People think boundary-setting is going to be this really big, tense awkward conversation like an intervention," she says. But in practice, "it's just saying 'no' to requests that make you uncomfortable right when the request happens." 

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," she says. 

Or, you could work with your child to chart a path toward financial independence over a defined period of time. 

Remember: Momentary guilt beats long-term resentment.

It's not uncommon to feel guilt when you say "no" to a family member's request for financial help. This can be especially true among women

"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. 

Become OK with upsetting other people.

People tend to struggle to say "no" to family members in need because they don't want to upset them or risk damaging the relationship. But upsetting people is a natural side effect of having boundaries.

"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.