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Played by: Katy Mixon
- Break the Haughty: Katie makes it her mission in life to take smug people down by a few pegs and, living in Westport, she is spoiled for choice when it comes to targets.
- Harmful to Minors: She's very lenient towards Anna-Kat, allowing her youngest to watch films with mature themes, to Greg's chagrin.
- How the Mighty Have Fallen: She sees living in Westport as this, saying she used to be quite popular back home but is an outsider here.
- Mama Bear: She's not afraid to take you to the ground, as Oliver's ballet teacher learned when she relentlessly picked on Oliver, assuming he was yet another spoiled Westport brat.
- Parental Substitute: Finds she's this to Cooper (Oliver's snobby friend) in Season 2. She can't stand him, but he really takes to her since his own parents are never around.
Played by: Diedrich Bader
- Adorkable: Greg is endearingly awkward and has certain character tics that Katie finds amusing.
- Clueless Chick Magnet: He has no idea, but a lot of the women in Westport are attracted to him because of how nice he is and are hoping Katie dies relatively young so they can have a chance at wooing him.
- Epic Fail: In "Boo-Who?", he attempts to tell off Chloe Brown Mueller for making Katie feel bad. However, in addition to being nervous, he was in a Frankenstein's monster costume at the time, so he was pretty tired and sweaty by the time he got to Chloe's store. Some of the costume's make-up got in his eyes, he tripped, and caused a chain of accidents that destroyed the store merchandise. Unsurprisingly, Katie is nonetheless thrilled by that.
- Friend to All Living Things: Greg bought a special grill to roast a pig, but he just didn't have the heart to kill and cook the little guy.
- Henpecked Husband: So much so that "The Pig Whisperer" sees everyone acknowledge that he always caves in to Katie, and he is determined to stand his ground for once.
- Nice Guy: Greg's kindness and attentiveness as a husband and father have garnered the attention of more than a few Westport women. Apparently Doris gets first crack at him in the event Katie dies young.
- "Well Done, Son!" Guy: "Family Secrets" shows him quite eager to please his parents, but he desperately wants the approval of his father, Thomas. It gets progressively deconstructed, as Thomas continually proves cold to Greg's overtures. Then it's revealed that Thomas had an affair in England and has had a second son for 20 years, so Greg finally blows up at him.Greg: My whole life, I've looked up to you. In my eyes, you couldn't do anything wrong. In your eyes, I couldn't do anything right! Well, it turns out I did everything right!
Played by: Meg Donnelly
- Bratty Teenage Daughter: Realistically portrayed. She's reached an age where she wants much more independence but her parents are reluctant to grant it so they clash. Katie even spends an entire episode wondering what happened to the sweet little girl Taylor used to be and decides to infect her own daughter with head lice to force mother-daughter bonding time.
- Everyone Loves Blondes: Dyes her hair blonde in one episode without Katie's permission.
- Hidden Depths: In Season 1, she befriends Viv not because of the snobbish lifestyle, but out of sympathy. Viv's husband is never around and the stepchildren revile her.
- What the Hell, Hero?: After she ditches her one true friend in Westport to hang out with popular girls, Greg gives her an angry dressing down, saying that her actions showed a fault in her character.
Played by: Daniel DiMaggio
- Ballet Episode: Takes up ballet in Season 1 purely as a strategic move to earn a scholarship to Harvard. Actually enjoys doing it, however, and, as of Season 2, is attending more advanced classes in Norwalk.
- Heel Realization: In Season 2, he seeks to befriend Spencer Blitz, a disgraced but wealthy former investor, in the hopes of getting into his will. "Family Secrets" shows that it's working, but hearing Spencer refer to him as like family causes Oliver to feel guilty about what he's been doing.
- Heterosexual Life-Partners: With Cooper.
- Intergenerational Friendship: He becomes quite close to Spencer Blitz, enough for the older man to declare that Oliver is his family.
- Jerk with a Heart of Gold: Oliver can be a brat at times, but he cashed out his business partner, Viv's housekeeper Luz, using his cherished savings so she could return to her native country and be with her young daughter.
- Like Father, Unlike Son: A number of episodes highlight how his personality and quirks clash with Katie and Greg, particularly his desire to become rich. Greg admits he and Katie have discussed the possibility that Oliver was Switched at Birth.
- Only Sane Man: With the exception of when he is focused on money and/or wealth, Oliver is the most level-headed member of the family as he is able to see past and call out the quirks and eccentricities they display.
- Screams Like a Little Girl: So much so that Katie mistakes Oliver's screams for Anna-Kat's.
- Young Entrepreneur: Oliver, upon finally realizing that his parents won't simply buy him whatever he wants, starts a lucrative career repairing and selling defective designer shirts and enlists the local housekeepers to to do the repair work.
Played by: Julia Butters
- All Girls Like Ponies: She desperately wishes own a pony and has a large collection horse-themed toys.
- Harmful to Minors: The reason she named the pet pig Hans Gruber is because Katie let her watch Die Hard.
- Parental Favoritism: Katie makes it fairly obvious that Anna-Kat is her favorite, much to Taylor and Oliver's chagrin.
- Super OCD: The Ottos moved to Westport so that Anna-Kat could attend a local school with an excellent special needs program.
- Wounded Gazelle Gambit: Season 2 revealed she was actually more adept at doing things for herself than previously thought, but she pretended otherwise so she wouldn't have to.
Played by: Ali Wong
- Children Are a Waste: This is what she feels about her unexpected pregnancy in Season 2 as it delays her plans to retire to a small Mediterranean island by several years, thus lowering her chances of still having her looks and seducing a well-built local when she finally does get there.
- Education Mama: In classic Asian Tiger Mom fashion, Doris is intent on her children excelling in everything they do and exerts enormous pressure on them as a result.
Played by: Carly Hughes
- Lipstick Lesbian: She used to be married to a woman named Celeste and the divorce has not been amicable.
- Open-Minded Parent: Her child-rearing philosophy is to engage her children as equals and to acknowledge their wants and desires through intellectual discussion. Brief glimpses at her home life shows that this has failed spectacularly.
- Color Blind Confusion: Admits he's this, which is why all of his "punch Porsches" are grey.
Played By: George Hamilton
- Cruel to Be Kind: He ultimately decides not to leave Oliver his millions. He knows that might seem harsh, but he feels that would rob Oliver of the joy of becoming rich on his own. Oliver agrees with this.
- Disco Dan: Still lives like it's The 80s. Justfied, as he'd been in prison for over 20 years and hasn't had much contact with the outside world.
- Expy: Of Gordon Gekko, Played for Laughs.
- Intergenerational Friendship: Develops one with Oliver, becoming a mentor to him.
- Killed Off for Real: Dies in the aptly titled episode "It's Hard to Say Goodbye".
- Freudian Excuse: He grew up being part of the richest family in town. That explains his poor people skills, but he says it's also why he doesn't care that Oliver is substantially poorer than he is. Everyone else is already poorer than he is, so he has no reason to care about stuff like that.
- Heterosexual Life-Partners: With Oliver.
- Hidden Depths: The richest kid in town cares way less about class differences than a lot of the adults.
- Lonely Rich Kid: Double subverted. While he acknowledges his parents are always away, he often seems blissfully unaware of why that's a bad thing. Season 3's "Insta-Friends" shows this is more of a Stepford Smiler attitude; his parents bail on him at literally the last minute for a social function, and he suffers a major depression.
- Rich in Dollars, Poor in Sense: Often unaware of anything he says that might be insulting or out of touch.
- Glamorous Single Mother: Subverted in Season 3. She is a constant wreck and exhausted from the baby's needs, as well as regularly going to Katie for help. She considers getting back together with her ex just to take the pressure off.
- Token Good Teammate: For the rich women in town. She's a snob and often thoughtless, but she's rarely malicious and actually likes Katie. Several of her appearances also portray her sympathetically, such as having a neglectful husband and a couple stepchildren who hate her.