High Maintenance Web Series, Season 5-6

The guy plays matchmaker, sending two middle-aged marijuana enthusiasts on a first date.

A woman struggles with her fiancé's increasing paranoia and survival tendencies.

A frustrated cubicle-working idealist tries to make a difference in the world by becoming a teacher. His attempts fall flat and the experience challenges his optimism.

Reagan and Ezra get priced out of Williamsburg and head to a more affordable neighborhood where they learn you can't have it all when it comes to New York real estate.

A hapless weed delivery girl fumbles her way through various misguided pursuits and steals some of the Guy's customers along the way.

Six friends escape the city and head upstate for a weekend, but they spend more time worrying about their careers than enjoying themselves.