Jules Cobbs (Courtney Cox)Courteney Cox portrays Jules Cobb, a recently divorced single mother exploring the truths about dating and aging. Jules spent her 20s raising a child and married to Bobby. She tries to relive her 20s and make up for lost time by dating younger men. She resides in a small town in Florida and is a real estate agent who is successful in business. Even though she has been out of the dating world for a while, Jules decides to find love again while living with her teenage son.
Ellie Torres (Christa Miller-Lawrence)Christa Miller portrays Ellie Torres, Jules' next door neighbor and best friend. Ellie is married to Andy Torres, and the two have a son Stan. She is the sarcastic, unapologetic confidante content who is often jealous of Jules' young assistant and friend, Laurie. She also loves to gossip but feels that Jules' new lifestyle is coming between their friendship.
Laurie Keller (Busy Philipps)Busy Philipps portrays Laurie Keller, Jules' young feisty employee who is known for her fun-loving personality. Laurie works with Jules in the same real estate office as her assistant. She encourages Jules to get out and have some fun and tries to reacquaint her to the world of dating. She considers herself Jules' best friend although Jules' best friends is Ellie who is often jealous of their friendship. She also enjoys spending quality time with her recently on and off boyfriend.
Bobby Cobb (Brian Van Holt)Brian Van Holt portrays Bobby Cobb, Jules' unemployed ex-husband who currently lives in his boat. Bobby is a classic under-achiever who’ll test Jules' patience as they attempt to raise their teenage son, Travis. He spent most of their marriage touring with his unsuccessful band and now spends his time cutting the grass at his son, Travis' high school.
Travis Cobb (Dan Byrd)Dan Byrd portrays Travis Cobb, is Jules' 17-year old son. He loves both of his parents although is constantly embarrassed by both of them. At school, he constantly deals with humiliation from his friends and classmates. He is generally supportive of his mother, but feels that her dating exploits cause him embarrassment. After dealing with his mom's real estate ads around town and his dad's new job as his school's lawn mower, his father helps him realize not to worry about what other people think.
Grayson Ellis (Josh Hopkins)Josh Hopkins portrays Grayson Ellis, a bartender and Jules' other neighbor. Grayson enjoys dating younger women and rubbing it in Jules' face. Grayson, like Jules, is also newly divorced, but unlike Jules, he embraces his bachelor and single lifestyle. However, he revealed that he wanted to have kids but his wife didn't want to have children with him.
Andy Torres (Ian Gomez)Ian Gomez portrays Andy Torres, Ellie's husband who is also Jules' next door neighbor. Andy is a devoted husband to Ellie and also a loving father to their son Stan. He loves his coffee and often spends time with Jules' ex-husband, Bobby.