Main cast
Courteney Cox as Jules Cobb – a recently divorced, single mother exploring the truths about dating and aging. Jules spent most of her 20s and 30s married to Bobby and raising a son, Travis. Because she has been out of the dating world for a while, Jules discovers it is difficult to find love again. At first, she tried to make up for lost time by dating younger men, thus becoming a "cougar", but the show quickly took a different turn as the character began to pursue men her own age. From the end of season 1, she began dating her divorced neighbor Grayson, whom she married in season 3. She resides in Gulfhaven, Florida and is a successful real estate agent. A close-up of her driver's license in a season 2 episode reveals her full first name to be Julia and her birth date to be November 15, 1968 (age 42 as of that season). Her self-centered, demanding behavior is usually overlooked by her friends and family, who balance it with her generosity and basic decency. Gregarious and optimistic, she's also an unapologetic anti-intellectual who loves wine and often drinks it out of an oversized glass, which she names. Her giant wine glasses (in order of appearance) are: Big Joe, Big Carl, Big Kimo (on vacation in Hawaii), then back to Big Carl, followed by Big Lou, Big Tippi, Big Sue, and Big Chuck. While she holds a pseudo-funeral for each broken glass, she quickly replaces them. She is often visited by her father, Chick, who is a widower since his wife, Jules's mother, died several years prior to the series. An only child, she often struggles with insecurity and abandonment issues.
Christa Miller as Ellie Torres – Jules's feisty next door neighbor and best friend. A former corporate attorney turned stay-at-home mother, Ellie is easily the most intellectual among the group. She is married to Andy Torres, and the two have a son named Stan. She is Jules's sarcastic, unapologetic confidante who takes pleasure in teasing Laurie, and to a lesser extent, Bobby, Grayson and Travis. Ellie's hard-polished guardedness belies a fierce loyalty. Ellie is a somewhat reluctant mother, demanding a nanny despite being a stay-at-home mom. She is usually quite dominant over Andy, who adores her. In season 6, she goes back to her corporate attorney job, after becoming bored and learning that Andy really wants to be a stay-at-home dad.
Busy Philipps as Laurie Keller – Jules's young attractive employee who is known for her fun-loving personality. Laurie works with Jules in the same real estate office, as her assistant. Prior to Jules's relationship with Grayson, Laurie encouraged Jules to get out and have some fun and tried to reacquaint her to the world of dating. Laurie has survived a rough childhood in foster care, and is initially a trashy party animal, but matures throughout the show as she learns how to become a functional grown-up. Ellie (who refers to her as "Jellybean") is initially openly hostile towards Laurie, but their relationship develops into a grudging respect and eventually a close, open friendship. She initially had many short-lived boyfriends and one-night stands, before enjoying a long-term relationship with young lawyer Smith Frank in seasons 1 and 2, and later a long-distance relationship with Wade, a soldier in Afghanistan, in seasons 3 and 4. She leaves Jules's employ and starts a successful cake shop in season 3. During season 4, she develops a crush on Travis, and they get together at the end of the season and date for the rest of the series. She and Travis have a son at the beginning of season 6.
Dan Byrd as Travis Cobb – Jules's and Bobby's son, who is a senior in high school at the start of the series, then later attends a local college. He loves both of his parents although he is frequently embarrassed by both of them. In high school, he dealt with humiliation from his friends and classmates but has made friends at college. He is generally supportive of his mother, but finds her parenting style a bit too smothering. After dealing with his mom's real estate ads around town and his dad's new job as his former high school's grass cutter, his father helps him realize not to worry about what other people think. Spending a lot of time with his parents and their friends, he often flirts with Laurie and is shown to have a crush on her. At the end of season 4 he gets together with Laurie. During season 5 their relationship is shown to be in constant competition with Jules and Grayson's, and he and Laurie have a son named Bobby at the beginning of season 6. He has a passion for photography and attends art college. Finding few career prospects after graduating college, he starts a mobile wine delivery business.
Josh Hopkins as Grayson Ellis – Owner of Gray's Pub, he lives across the street from Jules. Like Jules, he is newly divorced at the start of the series; unlike Jules, he embraced his newly single lifestyle. Early on, Grayson enjoyed dating younger women and rubbing it in Jules's face. Eventually, he revealed that he wanted to have kids but his ex-wife did not, a fact that becomes more painful when he learns that she and the man she left Grayson for are now expecting a child. He and Jules begin dating at the end of season 1, and in season 3, Grayson formally proposed marriage to Jules which she accepted. His desire to have children is a source of conflict with Jules until he discovers in season 3 that he has fathered a daughter, Tampa, during one of his post-divorce flings; he maintains an active role in Tampa's life, although this is seldom acknowledged in the show. He is a former model and aspiring but mediocre actor who plays guitar, and he often makes up songs about the group and reminisces about his acting days. He is nicknamed "Dime-Eyes" by Ellie, who believes his eyes are too small for his face.
Ian Gomez as Andy Torres – Ellie's husband who is also Jules's next door neighbor. Andy, an investment advisor, is a devoted husband to Ellie and also a loving father to their son, Stan. He and Jules's ex-husband Bobby are best friends, and Andy is shown to have a hero worship for Bobby. From season 4 until season 6 he is the mayor of Gulfhaven, although this is rarely mentioned and he often forgets that he has the position. Upon losing his job in season 6, Andy expresses a strong desire to be a stay-at-home dad, which results in Ellie going back to work.
Brian Van Holt as Bobby Cobb (seasons 1–5; guest season 6) – Jules's ex-husband who lives on his boat in a parking lot, which makes him legally homeless. Bobby married Jules after she became pregnant with their son, Travis. He was a professional golfer, and had numerous extramarital affairs during his career, which led to Jules divorcing him prior to the events of the pilot episode, although they still share a close friendship and even hooked up once. Bobby gives golf lessons and mows the lawn at Travis' former high school, and drives a well-worn golf cart. He frequently refers to Jules as "J-Bird". He also has invented a game, Penny Can, which is featured in several episodes. He has short-term relationships with Travis' photography teacher Angie in season 3 and surfing buddy Lisa Riggs in season 4. Van Holt exited the series at the beginning of the sixth season, as his character took a club pro job at a golf course in Georgia.
Bob Clendenin as Tom Gazelian (season 6; recurring seasons 1–5) – Jules's widowed neighbor who expresses his attraction for her in weird ways, makes wine in his garage, and is always doing things for Jules and the gang without getting anything back in an attempt to become part of their group. He is frequently found to be peering into Jules's kitchen window, unnoticed by Jules and/or the gang until he says something. By season 4 he is considered one of the gang, appearing in most episodes and accompanying the group wherever they go, although still generally standing outside Jules's window instead of in the kitchen with the others. His behaviour is often weird and creepy, and details of his otherwise normal and successful life (that he is a millionaire neurosurgeon, former all-state track star, with an adult son in the Marines and a daughter attending law school) are slowly revealed as the series progresses.
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