Michaela Watkins (Sydney) and Rob Delaney (Rob) have worked together before in the Funny or Die comedy shorts "The Ayn Rand Show" (2012) and "MA Men 2" (2010). The latter also featured Nat Faxon, who plays Sydney's boyfriend, Pat, in episode 6.
In 2018, Emily Lloyd-Saini (Tanya) performed on an episode of "Rob Delaney's Stand Up Central," a British comedy series that aired on Comedy Central.
Actor Daniel Lapaine (Dave) made his feature film debut in the popular "Muriel's Wedding" (1994) in his native Australia, where he graduated from the National Institute of Dramatic Art just two years before.
Ashley Jensen (Fran) found her breakout role in 2005 as Maggie in Ricky Gervais' BBC Two/HBO series "Extras," for which she won two British comedy awards and nominations from BAFTA and the Emmys.
Michaela Watkins, who plays Rob's sister, Sydney, spent time growing up not far from where Rob Delaney grew up in Massachusetts.