'Playboy Compass' was a British unrealised operation, originally designated 'Playboy' and then retitled 'Compass', to employ 'special means' (a double agent) to bring about the destruction of a U-boat (February/August 1943).

Intended for implementation off the coast of Lebanon in the eastern part of the Mediterranean Sea, 'Playboy-Compass' was to use false information passed to the Germans by a double agent ('Quicksilver' or 'The Pessimists' of Colonel Dudley W. Clarke’s 'A' Force Middle Eastern deception organisation) to lure a U-boat alongside a fishing boat fitted with a false explosive-filled keel, which would then by slipped to attach itself magnetically to the hull of the U-boat for later detonation. Considerable experimentation was undertaken, but the plan was never tried operationally.