A vessel bifurcation wire assist device and related methods of advancing guidewires into main and branch vessels of a vessel bifurcation. The wire assist device includes a first guidewire housing member defining a first guidewire lumen sized to advance over a first guidewire, and a second guidewire housing member defining a second guidewire lumen sized to advance over a second guidewire. The second guidewire housing member has a first directional arrangement and a second directional arrangement. The first directional arrangement provides a parallel arrangement of the second guidewire relative to the first guidewire housing member, and the second directional arrangement provides an angled arrangement of the second guidewire relative to the first guidewire housing member.