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First, wiggle the chair to find loose areas. Then examine the chair's assembly by turning it over and looking at all joints, screws, dovetailing and pegs.
If the hole is stripped and the screw can't be tightened, remove the screw, put a dab of wood glue into the hole, stick in a toothpick and break it off at the surface of the wood. Next, begin tightening the screw. The inserted toothpick will provide "bite," which will allow the screw to be tightened.
If a screw is missing, remove a screw and get another one the same size. It is also possible to use a screw that is slightly longer or thicker to provide better bite in an old hole.
Any or all of these techniques can be combined to create a distressed look: Start with the most brutal damage possible: filing a groove on one side. Pull the carpenter's razor against an arm or back to remove paint down to the bare wood. As an alternative method, remove paint with rough sandpaper in the areas where the chair would have gotten the most use. Use a hammer to dent the seat.
First, use the fine and finer grades of sandpaper to smooth all edges. Brush on stain wax to make crevices darker. To achieve a vintage appearance, use a wire brush to get the stain into the grain and any nicked or scratched areas. Finally, use steel wool to buff and remove any excess wax and stain from raised areas.