We invited men to discuss their volunteer careers with hospice-palliative care (HPC) to better understand how to recruit and train, retain and support, and then successfully end their volunteer experience. Nine male current or former HPC volunteers participated in face-to-face interviews which were transcribed and analyzed. The men described a complex interplay of individual characteristics with the unique roles available to HPC volunteers. The men’s recruitment experiences coalesced around both individually based and organizationally based themes. Results pertaining to retention revealed the interchange between their personalities, the perks and pitfalls of the unique experiences of an HPC volunteer, and the value of the organization’s support for these volunteers. Our interpretation of these experiences can help HPC organizations enhance their recruitment, retention, and support of male volunteers.