What washers are you taking about, the washers in the connectors for the tap? Are they flexi pipes or rigid tap connectors? If the former then check the old rubber washers and if they are ridged/marked quite badly then best to replace them. If the latter then new fibre washers every time.
Yep - new fibre washers every time. Just make sure you have all of the old washer off. Should always be able to draw the nut back enough to clear the whole flange, if not then the old washer's crushed in there and holding the nut.
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