Should I sue a family member over money they owe me?

The legal answer is straightforward and unhelpful: relatives are suable like anyone else, and the rules do not soften because of the relationship. The practical answer is harder, and pretending otherwise does nobody a service. Filing against a family member is close to irreversible socially, it becomes known across the family whether or not you want it to, and the sums involved in small claims seldom justify what gets lost. Anyone weighing this should price the relationship into the decision honestly rather than telling themselves it is only about the money, because that is rarely true and the regret usually arrives later.

There is a middle step that resolves a meaningful share of these, and it is underused because it feels confrontational. A short written request, stating what was lent, when, what remains outstanding and a specific date by which you would like it back, changes the character of the thing. It moves the money out of the category of a favour nobody wants to mention and into a defined obligation with a date attached, which is often all that was needed. Keep it factual and unemotional, since the letter may be read aloud in court later. If it goes entirely unanswered, you have learned something useful about how they see the debt, and the decision becomes considerably easier.