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Casey Wilson as Annie Fletcher Schuffman – Jake's fiancée and eventually wife, described as emotionally volatile and over-dramatic, in contrast to the more laid-back Jake. Now that Annie and Jake are engaged and living together, she's had a hard time getting adjusted to life as "engagedlyweds" and because of her emotional nature, she often gets easily stressed out, most notably when dealing with things such as when Jake moves in with her, getting along with Jake's mother, and having to host the family Thanksgiving for the first time as a couple. At the conclusion of the series, Annie finds out she's technically a Canadian and after failing her citizenship test to become an official American citizen, she has to quickly marry Jake before she's deported from the country.
Ken Marino as Jake Schuffman – Annie's fiancé and eventual husband, described as the more rational and level-headed in the couple, he is often forgiving of Annie's quirks and over-dramatic behavior. Now that Annie and Jake are engaged and living together, Jake tries to put Annie at ease during her constant freaking out over getting married and often has to act as a peacemaker between Annie and his mom, while also attempting to get to know Annie's dads better. Jake was previously engaged to a woman named Fantasia Yang, but called it off after he realized she was insane.
John Gemberling as Gil – Jake's mopey, depraved and divorced best friend who sells hair loss products. His friends are often concerned about him, as his life has mostly been a mess ever since his wife recently left him. It has also been shown that Gil relies too much on Jake as a friend, as the gang has made attempts to help Gil be less dependent on Jake.
Sarah Wright Olsen as Dennah – Annie's proudly single best friend who works as a pre-school teacher. She is said to have a "take it or leave it" attitude toward marriage.
Tymberlee Hill as Kay – Annie and Jake's lesbian friend and neighbor. Kay is shown to be sarcastic and eccentric, and often makes references to past romantic flings, such as hook-ups she made on "Boobr", a dating app for lesbians. Her full name is Kay Sedia (pronounced exactly like "quesadilla"). Kay has her first longterm relationship with a woman she meets named Hailey, after trying to keep their relationship a secret at first.
Dan Bucatinsky as Kevin 2 (episode 8, 10–18; previously recurring guest) – One of Annie's gay dads, both named Kevin. It's been said that Annie got her dramatic side from dads, who named her after the famous Broadway musical. Like Annie, the Kevins are also newly engaged.
Tim Meadows as Kevin 1 – One of Annie's gay dads, both named Kevin. Both of "The Kevins" often argue which one of them is her biological father, despite the obvious fact that "Kevin One" is African-American and Annie is white. Like Annie, the Kevins are also newly engaged.
