We start the investigation of free boundary variational models featuring oscillatory singularities. The theory varies widely depending upon the nature of the singular power \( \gamma(x) \) and how it oscillates. Under a mild continuity assumption on \( \gamma(x) \), we prove the optimal regularity of minimizers. Such estimates vary point-by-point, leading to a continuum of free boundary geometries. We also conduct an extensive analysis of the free boundary shaped by the singularities. Utilizing a new monotonicity formula, we show that if the singular power \( \gamma(x) \) varies in a \( W^{1,n^+} \) fashion, then the free boundary is locally a \( C^{1,\delta} \) surface, up to a negligible singular set of Hausdorff co-dimension at least 2.