A flexible optical probe that accomplishes wafer-level directional coupling of light into optical waveguides is investigated theoretically and experimentally. Simulated results indicate high coupling efficiencies in excess of 80% for a range of parameters. Probe fabrication was implemented using SU8 as flexible waveguide material. Coupling of light from flexible probe to an S-shaped test waveguide demonstrated 11% efficiency compared to direct butt coupling. These results may lead to increased yield, shorter development cycles and overall savings in PLC packaging costs.