Multiple guidewire systems and methods of using are disclosed. In one illustrative embodiment, a guidewire system may include a first guidewire releasably coupled to a second guidewire such that when the guidewire system is advanced through a vessel, the first guidewire may be coupled to the second guidewire. After the guidewire system has been advanced through a vessel, the first guidewire and the second guidewire may be separated. In some instances, the first guidewire may be chemically, mechanically, electrically, and/or mechanically releasably coupled to the second guidewire.