Chicago Party Aunt

Daniel Whiddington is explicitly identified as Diane's 18-year-old gay nephew, and his character arc is not centered around coming out but rather his journey into adulthood. In Season 2 (Part 2), Daniel engages in an intimate relationship with a professional baseball player named Jason, which explores themes of public versus social acceptance of same-sex relationships. Diane inadvertently outs Gideon, her gay boss at the hair salon, to his mother in one episode, which causes Gideon distress.

The show features 'inappropriate references to sex and cartoon nudity' and includes mentions of 'oral sex twice, among other rapid fire sex jokes.' Aunt Diane gives her gay nephew Daniel a flask that, when tipped, reveals a cartoon picture of a man becoming fully nude on screen. In Episode 2, Diane is caught sleeping commando in a mini skirt by her sister Bonnie, and a similar instance occurs with a random customer. Daniel's parents, Bonnie and Mark, are shown discussing their fertility treatments in front of Daniel and his boyfriend Jason.

In the premiere episode alone, the 'f-word is used six times, the s-word seven,' along with other vulgarities such as 'a–' and 'b–ch.' The show also includes 'crude terms for the male anatomy and female anatomy, as well as references to bodily functions,' and someone is called a 'whore.' Diane is noted for 'drop[ping] plenty of F-bombs' as part of her character's speech.

Heavy drinking is portrayed as Aunt Diane's 'primary 'hobby',' and the show depicts intense partying, individuals throwing up, and hangovers. Diane's ex-husband, Kurt, mentions her drinking 'a whole bottle of brandy in one night,' and she is seen getting multiple kegs for parties and smoking. The dialogue also explicitly discusses 'smoking, steroids, and heroin smuggling.' Diane's personal mantra reflects this, often quoted as, 'If life gives you lemons, turn that shit into Mike's Hard Lemonade.' She is also known to 'never turns down a shot of Malört.'

Diane Dunbrowski consistently 'avoids adulting' and is frequently shown to 'lie and act selfishly in almost every situation,' indicative of a rebellious and defiant attitude. Daniel decides to take a gap year and live with Diane instead of attending Stanford University, going against the wishes of his 'uptight' and 'strait-laced' mother, Bonnie, who expresses 'chagrin' over his decision. Diane also displays direct disrespect, such as making a crude comment to her sister Bonnie, asking 'Did you just get laid?' after a heartfelt moment.