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Make sure to stop in on either a Thursday or Sunday night for Karaoke night. 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.
Guest commentaries on the show written three of Cox's former Ups co-stars: Every year we put together a definite review of all the unique women to dating a proper and they have been the head for a while.
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. 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' 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. Carolyn Hennesy as Barb Coman season — a man-hungry older cougar who is a competitor of Jules in real estate.
She usually appears briefly to deliver a lascivious Meet moms and cougars from ohio city colorado. As Jules observes in one episode,  "do you just follow me around, waiting to say things? Ken Jenkins as Chick season — Jules' father who is a keen lover of horses and whose favourite holiday is Halloween. Chick officiates Grayson and Jules' wedding in the season three finale after becoming ordained as a minister online. In season four he is diagnosed with Alzheimers' disease, after complaining about his memory worsening for some time, and he moves in with Jules in season 5 to allow her to watch over him.
Nick Zano as Josh season 1 — a younger man who had dated Jules, but who she felt wanted a more serious relationship than she did. Later Jules decided to break up with him due to his desire for a serious relationship. The actor Nick Zano left the show due to his offer on Melrose Placewhich was later cancelled. Spencer Locke as Kylie season — Travis' girlfriend at the start of the series. Travis loses his virginity to Kylie, but the two later break up after they both cheat on each other with Travis kissing Heather Spangler and Kylie kissing Joey Spangler.
The couple later reconciles and continues to date into Season 2, even though Kylie reveals that she no longer wants to be exclusive with Travis. They break up for good when Travis meets his first college girlfriend. In Season 2, Smith breaks up with Laurie after she admits to Jules that she is in love with him and he realizes he doesn't feel the same way. Still, he represented the longest and most serious relationship that Laurie had had up to that stage in her life. Barry Bostwick as Roger Frank season5 — a wealthy businessman and Smith's father. He strongly disapproves of Laurie, receives golfing lessons from Bobby, and eventually buys "Penny Can" from both of them.
In Season 3, he marries Barb Coman. Roger was the mayor of Gulfhaven until Andy's election. LaMarcus Tinker as Kevin season — Travis' college roommate and friend.
Travis annoys Kevin when they first meet, as he's trying to find his way in college. However, Travis earns Kevin's respect and they become good friends. Collette Wolfe as Kirsten season 2  — Travis' new, slightly older girlfriend, whom he met in his first semester of college. When she revealed she was moving away, Travis impulsively proposed to her, but she immediately rejected him and was not cougads again on the series. Sheryl Crow as Sara Kramer season 1 frkm — a likeable and sexy wine vendor whose semi-serious relationship with Grayson was his first with a woman his age after his post-divorce period of targeting younger, naive girls for affection.
Sara breaks up with Grayson after it becomes clear that he also has feeling for Jules. David Clayton Rogers as Matt season — Matt appears in the pilot episode who Jules meets at a bar and spills wine over. Matt is Jules's lover and is the first person she sleeps with after her divorce and therefore becoming a 'cougar'. The character of Matt appears in season two as a friend of Grayson's unknowingly to Jules, when Grayson learns that they have slept together. Gloria Garayua as Rosa season 2 — Stan's babysitter employed by Ellie and Andy to care for their son. Rosa was a recurring character often mentioned and seen during season two.
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