A family member keeps asking me for money and I don't know when to help and when to say no.

“He that is surety for a stranger shall smart for it: and he that hateth suretiship is sure.”

Proverbs distinguishes between genuine generosity and financial entanglement that creates dependency or resentment. The proverb speaks of guaranteeing a stranger's debt, but its caution applies wherever money and relationship tangle, and family systems carry complex dynamics that pure charity does not. It is not unloving to think carefully before giving.

“Bear ye one another's burdens, and so fulfil the law of Christ. For if a man think himself to be something, when he is nothing, he deceiveth himself. But let every man prove his own work, and then shall he have rejoicing in himself alone, and not in another. For every man shall bear his own burden.”

Paul uses two different Greek words here: one for a crushing burden too heavy for one person, and one for a soldier's standard-issue pack. We are called to help with the former, not to take over the latter. The distinction matters enormously in family financial dynamics: there is a difference between helping someone survive a crisis and funding a lifestyle that avoids responsibility.