Andrew Rannells Helps a Grieving Allison Janney Plan a Funeral in Heartfelt Miss You, Love You Trailer

Andrew Rannells says getting to work with Allison Janney "felt like I had won the gay acting lottery" in their new movie, which debuts on HBO May 29.

Andrew Rannells and Allison Janney are two strangers forced to confront death and the complications of life together in their new movie.

PEOPLE is debuting the trailer for HBO's new movie Miss You, Love You, directed and written by Academy Award-winning screenwriter Jim Rash (The Descendents, The Way Way Back) on Wednesday, May 20. In the film, Rannells, 47, portrays a man named Jamie, a personal assistant to a successful journalist, who travels to help his boss' estranged mother, Diane (Janney), arrange her husband's funeral.

Forced to grieve alongside a stranger, Diane and Jamie navigate her state of mind following her husband's death and both of their relationships with Diane's estranged son in the days that follow.

"A blunt, grieving widow, Diane Patterson is forced to plan her husband's funeral with a total stranger: her estranged son's assistant, Jamie Simms," reads an official synopsis for the movie. "As they fumble through grief and their strange, darkly funny circumstances, buried secrets and long-held resentments surface, but their partnership becomes an unlikely conduit for connection, laughter, and healing for this mother and her unexpected surrogate son."