The first example for the ruthenium‐catalyzed ligand‐directed meta‐selective C−H mono‐ and difluoromethylation is developed, affording a variety of new meta‐mono‐ and difluoromethylated 2‐phenylpyridines, 2‐phenylpyrimidines, and 1‐phenylpyrazoles in moderate‐to‐good yields. This new transformation exhibits broad substrate scope, good functional group tolerance, and high efficiency, and offers a practical approach to synthesize mono‐ and difluoromethylated arenes. Mechanistic studies indicate that a reaction pathway involving palladium‐initiated radical species is involved in the catalytic cycle. The new dual catalytic system consisting of compatible ruthenium(II) and palladium(0) complexes enables the key processes of C−H activation and mono‐/difluoromethyl‐radical formation to occur and achieves the meta‐selective functionalization efficiently. In addition, the present protocol can also be extended to non‐fluoromethylation. A meta approach to fluoromethylation: The first example for the ruthenium‐catalyzed ligand‐directed meta‐selective C−H mono‐ and difluoromethylation is developed, affording a variety of new meta‐mono‐ and difluoromethylated 2‐phenylpyridines, 2‐phenylpyrimidines, and 1‐phenylpyrazoles in moderate‐to‐good yields. This new transformation exhibits broad substrate scope, good functional group tolerance, and high efficiency, and offers a practical approach to synthesize mono‐ and difluoromethylated arenes.