Main •
Carly Craig as Olivia Maple, a life insurance broker at Wilson and Hines Insurance company. While out celebrating her 35th birthday, her sister downloads Tinder to her phone and she proceeds to swipe right on numerous men while in a drunken stupor. She awakes the next morning to discover that she now has 252 matches and makes the decision to go out with every one of them. •
Rosanna Arquette as Mary Maple, Olivia and Jayne's widowed mother. Her husband of 34 years died of a heart attack during a golf lesson and she now lives with Olivia. She's trying to become a more independent person going so far as to get her first job working at a clothing store. •
Chelsea Frei as Jayne Tyler, Olivia's married sister who just gave birth to a daughter. She struggles with figuring out her own identity separate from marriage and child and feels like her husband hasn't looked at her the same way since she gave birth.
Recurring • Craig Frank as Dr. Jim Tyler, Jayne's husband and a gastroenterologist. He begins to fear losing his job after failing to bring enough new patients into his practice due to some bad Yelp reviews. This causes him to become more distant towards Jayne leading to a falling out between them after he discovers she was flirting with a man on her sister's Tinder account. • Zaire and Zamir Salazar as Abby Tyler, Jayne and Jim's infant daughter. •
Alice Lee as Britney, the manager of the clothing store Rock Etiquette. She helps style Mary and takes new pictures of her for her dating app accounts. She and Mary go on to become friends and she hires her to work at the store as an employee. The pair ultimately decide to move in together after Britney kicks out her previous roommate. • Miguel Pinzon as Danny, Olivia's receptionist whom she seeks advice from and gossips with. •
Rhys Coiro as Charlie, a history teacher that Olivia matches with on Tinder. Jayne flirts with him using Olivia's account and pretends to be her. He and Olivia eventually begin to date and she comes clean about her sister's deception. The couple breaks up after Olivia admits that she is not sure she wants kids while he is certain that he does.
Guest •
Jason Sudeikis as Dr. David Bennett ("Matching Up"), a gynecologist that fills in for Olivia's regular doctor. •
Thomas Lennon as Aaron Cunningham ("Matching Up"), the CEO of Cunningham Insurance company and a man that Olivia matches with on Tinder. •
Tyler Posey as Griffin ("Baby Steps"), a personal trainer and gym owner that Olivia matches with on Tinder. •
Christopher McDonald as Mary's One Night Stand ("Baby Steps"), a man that Mary meets while out eating dinner by herself and with whom she later has sex. •
Charles Michael Davis as Josh ("Deal Breakers"), a lawyer and sex addict that Olivia matches with on Tinder. •
Robert Pine as Ethan ("Deal Breakers"), a widowed man living on a houseboat that Mary matches with on Oomph and with whom she goes on a date. •
Rick Springfield as himself ("The Rock Star"), a famous 80s musician that Mary matches with on an exclusive dating app that includes celebrities. •
Penny Johnson Jerald as Cynthia Tyler ("The Rock Star"), Jim's mother and a real estate agent that lives in San Francisco. She is often passive aggressive towards Jayne and suggests that she get a nanny when she comes to visit. • Andy Gala as Dr. Bradley Navin ("The Rock Star"), a doctor that works in Jim's practice who is set up on a date with Olivia. •
Bryan Greenberg as Ryan ("The Ex"), Olivia's ex-boyfriend that founded a charity, Meals with Feels, that feeds homeless people on Saturdays. He went to college with Jim and plays on a soccer team with him. • Michelle Hayden as Lexi ("The Ex"), Ryan's pregnant girlfriend with whom he founded his charity. •
Barry Livingston as Teacher ("The Ex"), an instructor teaching a course on various computer programs that Marry attends. •
Marc Evan Jackson as Dr. Singer ("The Party"), a doctor at PCR Fertility Clinic who Olivia consults with regarding freezing her eggs. •
Sarah Burns as Nicole ("The Party"), a woman that Olivia meets using the friend option on a dating app that she attends a concert with. •
Peter Gallagher as Andrew ("For A Nickel I Will"), a retired lawyer that comes into Rock Etiquette shopping for his granddaughter. He and Mary begin dating but decide to stop seeing each other as she is focused on her new job whereas he wants to take advantage of his retirement. •
Jon Ecker as Bobby Garcia ("Hard Maybe"), a guy that Jayne had a crush on in high school and whom she referred to as "Hot Jesus". She reconnects with him at a bar years later and ends up making out with him in his car. ==Episodes==