The synergistic solubilization of two major hydrophilic (vitamin C, ascorbic acid, AA) and lipophilic (vitamin E, D-alpha-tocopherol, VE) antioxidants within reverse hexagonal (H(II)) mesophases is reported. The H(II) mesophases are composed of monoolein (GMO)/VE/AA/water. A wide range of VE concentration was examined (on the expense of GMO concentrations) while the AA and water concentrations remained constant (4 and 12.5 wt %, respectively) in order to expand the H(II) mesophase. SAXS and DSC combined with ATR-FTIR techniques were utilized to study the interactions between each solubilizate and the H(II) component that enabled the synergistic accommodation of the hydrophilic and hydrophobic molecules. It was revealed that up to 27 wt % VE solubilized within the H(II) mesophase. This hydrophobic additive localized at the lipophilic GMO tail region solvating the surfactant tails, thereby enabling the formation of the H(II) structure. As a result, the lattice parameter and the melting point of the hydrophobic tails decreased. Above 27 wt % VE (up to 33 wt %), once the GMO lipophilic region was homogenously solvated, additional VE molecules located closer to the interface. At this range of concentrations, new hydrogen bonds between O-H groups of VE and O-H groups of GMO were formed. Once 35 wt % VE was introduced, the H(II) structure transformed to face-centered reverse micellar cubic phase (Fd3m, Q(227)).