Cougar Town
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50 free Cougar Town trivia questions with answers — trivia quiz, new questions added Oct 2026.
Cougar Town ran for six seasons across two networks and spent most of them apologizing for its own title. What began as a comedy about a divorced Florida mom re-entering the dating scene quickly became a warm, wine-soaked hangout show about a group of neighbors who simply refuse to leave each other alone. This quiz covers the people and the running jokes: Jules Cobb and her oversized glassware, her ex-husband's odd living arrangements, the invented games, the nicknames, the weddings and the surprise guest stars from other famous sitcoms. A few questions go behind the scenes, to the creators, the casting and the long campaign to rename the series, and several come from the season 2 holiday episode When the Time Comes. It is written for fans who watched the whole run and for anyone who remembers the show mainly as the one with the giant wine glass. Every answer comes with a short explanation, so you will leave knowing more than you arrived with.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Nearly every Cougar Town episode takes its title from a song by which Florida-born rock star?
Tom Petty
Tom Petty, born in Gainesville, lent his song titles to all but two episodes: the pilot and one named after a duet performed on screen.
Q 02Jules Cobb drinks from a series of giant wine glasses on Cougar Town; what does she call the first?
Big Joe
Big Joe heads a long line of named glasses, and Jules holds a mock funeral whenever one breaks before swiftly replacing it.
Q 03On Cougar Town, what is the name of the game Bobby Cobb invents and later sells to a businessman?
Penny Can
Penny Can starts as a pastime for the gang, is bought by Roger Frank's company, and by season 5 is paying Bobby royalties from abroad.
Q 04Within the sitcom Cougar Town, why is the Florida hometown of Jules Cobb nicknamed after a cougar?
The high school mascot
The high school mascot is the excuse, a device co-creator Bill Lawrence admitted was a big cheat before the pilot had even aired.
Q 05Which cable network rescued Cougar Town for three more seasons after ABC canceled it in 2012?
TBS
TBS stepped in just two days after the cancellation and eventually aired as many seasons as the original network had.
Q 06Which Friends actress plays Glenn, therapist to Jules Cobb, in the season 2 premiere of Cougar Town?
Jennifer Aniston
Jennifer Aniston was the second of three Friends alumni to drop by, after Lisa Kudrow in season 1 and before Matthew Perry in season 5.
Q 07In Cougar Town's two-part season 2 finale, the gang flies to which state to bring Travis Cobb home?
Hawaii
Hawaii is where a heartbroken Travis flees after dropping out of college, and the rescue mission doubles as a group vacation.
Q 08On Cougar Town, newly divorced Jules Cobb supports her son Travis by working in which profession?
Real estate agent
Real estate agent Jules has her photo on signs all over town, which mortifies Travis when younger kids start stealing them.
Q 09On Cougar Town, Bobby Cobb is legally homeless because he lives in a parking lot aboard what?
A boat
A boat stranded on dry land is home for Bobby, and the lot around it later hosts a friend's wedding.
Q 10In which fictional Florida town, home to Jules Cobb and her wine-loving friends, is Cougar Town set?
Gulfhaven
Gulfhaven sits in Sarasota County on the Gulf Coast, and the opening credits pinpoint the area on a map of the state.
Q 11Which Freaks and Geeks alumna plays Laurie Keller, assistant to Jules Cobb, on Cougar Town?
Busy Philipps
Busy Philipps won a Critics' Choice Television Award for the role and directed an episode in the final season.
Q 12Which Cougar Town star is married to co-creator Bill Lawrence, who created Ellie Torres for her?
Christa Miller
Christa Miller had a recurring role on Scrubs too, and her husband jotted down little things she said to use for Ellie.
Q 13Which actor plays Grayson Ellis, the guitar-strumming bar owner Jules Cobb marries on Cougar Town?
Josh Hopkins
Josh Hopkins went on to direct for the sitcom, while Grayson, a former model, keeps making up songs about his friends.
Q 21In Cougar Town's When the Time Comes, which Scrubs star appears as himself inside a phone app?
Zach Braff
Zach Braff pops up twice as the voice of a phone app that suggests which appetizers to order.
Q 22Jules Cobb hosts a romantic dinner in Cougar Town's When the Time Comes hoping Grayson will do what?
Say he loves her
Say he loves her is all Jules wants from the meal, while Ellie and Laurie spend the same episode crushing Andy's optimism.
Q 23Which character, the ex-wife of Grayson Ellis, first appears on Cougar Town in When the Time Comes?
Vivian
Vivian left the marriage saying she did not want children, then got engaged to another man and became pregnant, a crushing blow for Grayson.
Q 14Which My Big Fat Greek Wedding actor plays Andy Torres, devoted husband of Ellie, on Cougar Town?
Ian Gomez
Ian Gomez was married to that film's writer and star, Nia Vardalos, who guest-stars on the sitcom as Andy's flirtatious sister-in-law.
Q 15Which Scrubs veteran plays Chick, the horse-loving father of Jules Cobb, on Cougar Town?
Ken Jenkins
Ken Jenkins first appears for Halloween, Chick's favorite holiday, and later gets ordained online to marry his daughter to Grayson.
Q 16Which Scrubs star plays Angie, the college teacher who dates Bobby Cobb in season 3 of Cougar Town?
Sarah Chalke
Sarah Chalke's arc ends when Bobby wants to be exclusive and Angie turns out to have expected only a fling.
Q 17Which singer guest-stars in Cougar Town's first season as Sara, a wine rep who dates Grayson Ellis?
Sheryl Crow
Sheryl Crow sings a duet with Grayson during her arc, and that song gave the episode Everything Man its title.
Q 18Which Hitchcock leading lady appears as herself in Cougar Town's season 4 finale to cheer up Chick?
Tippi Hedren
Tippi Hedren is one of Chick's favorite stars, so the gang cancels a trip to the Bahamas and takes him to Hollywood to meet her.
Q 19Cougar Town came from a company Courteney Cox ran with which Scream co-star, then her husband?
David Arquette
David Arquette was an executive producer and guest-starred in the season 3 finale as a hotel concierge, by which time the couple had separated.
Q 20Cougar Town's season 2 episode 9, When the Time Comes, takes place on which holiday?
Thanksgiving
Thanksgiving also falls in the ninth episode of season 1, when another romantic dinner planned by Jules backfires.
Q 24On Cougar Town, the feared Dr. Amy Evans, played by Lisa Kudrow, practices which medical specialty?
Dermatology
Dermatology is worth the abuse to Jules and Ellie because Dr. Evans is the best in town, until Jules learns the doctor is dating Bobby.
Q 25On Cougar Town, Jules Cobb agrees to date Matthew Perry's wealthy Sam after doing what to him?
Crashing into his car
Crashing into his car while reaching for her slipped wedding ring leaves an uninsured Jules at Sam's mercy, so a date buys his silence.
Q 26Which Community character, a Cougar Town fan played by Danny Pudi, cameos in the season 2 finale?
Abed Nadir
Abed Nadir eavesdrops on Laurie and Travis and then runs off, paying off a Community joke in which he claimed a walk-on role.
Q 27Community imagined a British original of Cougar Town whose title riffs on which period drama?
Downton Abbey
Downton Abbey inspired the spoof, and the sitcom returned the joke with a season 3 title card welcoming viewers to the fake show.
Q 28Barry Bostwick, Roger Frank on Cougar Town, starred in which earlier Bill Lawrence sitcom?
Spin City
Spin City alumni Alan Ruck, Richard Kind and Michael McDonald all turned up in guest roles as well.
Q 29Co-creator Bill Lawrence makes a cameo in Cougar Town's season 3 finale playing what?
A police officer
A police officer arrives to shut down the ceremony for breaking a local ordinance, so the guests keep moving the wedding along to dodge him.
Q 30Bobby Cobb, the laid-back ex-husband on Cougar Town, once toured as a professional in which sport?
Golf
Golf kept Bobby on the road, where his many affairs ended the marriage, and he later scrapes by giving lessons and mowing lawns.