How do I choose the right filing status when more than one seems to fit?

Filing status flows mostly from your situation on the last day of the year. If unmarried and supporting a qualifying dependent while paying more than half the home's costs, head of household usually beats single because it offers a larger standard deduction and wider brackets. Married couples almost always do better filing jointly than separately. A recently widowed person with a dependent child may use qualifying surviving spouse status for two years to keep joint-like benefits. When two statuses seem possible, compute the tax both ways; software makes this easy. The IRS provides an 'What Is My Filing Status?' interactive tool. Picking the most advantageous status can save hundreds or thousands, so it is worth the few minutes.