After reviewing the group structure and representation theory for the dihedral group $D_{2n},$ we consider an intertwining operator $Φ_ρ$ from the group algebra $\mathbb{C}[D_{2n}]$ into a corresponding space of semi-magic matrices. From this intertwining operator, one obtains the generating function for enumerating the associated semi-magic squares with fixed line sum and an algebra extending the circulant matrices. While this work complements the approach to $D_{2n}$ through permutation polytopes, we use only methods from representation theory.