Ellen decides to go out more as part of her New Year's Resolution. However Ellen's plans for a solo grand dinner at a fancy restaurant doesn't go well as planed and she decides to take pottery lessons instead. Meanwhile, Paige's kitchen goes up in flames after Spence and Joe house sit for her while she's in Canada during a movie location shoot.
Ellen decides to add a new section onto her new house but has to wait nine months for a construction permit. Joe helps Ellen by asking his latest girlfriend, a wealthy older woman named Madeleine, for help since she knows some city officials. When Ellen tells Joe that she thinks that dating Madeleine makes him a kept man, Joe breaks up with her who responds by taking away Ellen's construction permit. When Ellen tries becoming chummy to Madeleine to give back her construction permit, Joe realizes that Ellen's bonding with Madeleine makes her a kept woman. Meanwhile, ...
After donating some blood to a blood bank, Ellen goes out with Spence to a wine tasting party where she gets tipsy from consuming too much wine and her outrageous behavior costs Spence the promotion he has been seeking when she offends his superior, the hospital chief-of-staff. But when Ellen returns the next day to apologize to the doctor at the hospital, he takes thinks the wrong way and makes a pass at her. Meanwhile, Joe writes jokes for Audrey's comedian boyfriend Mike. But Joe's Canadian humor falls flat with the American audience. So, Joe takes Mike to his ...
On Ellen's 35th birthday, she and the gang go to the rock 'n roll music camp in Hollywood where they get to jam in a band with David Crosby, Aaron Neville and Bonnie Raitt. But Ellen gets cold feet when she feels her singing can't compare with theirs.
Ellen helps Peter prepare a production of Romeo and Juliet done by deaf actors. Audrey, now single after breaking up with Mike, takes a liking to Brian, the actor who is playing Romero. But as result of a misunderstanding of sign language, Ellen thinks Brian is making a pass at her. Meanwhile, Spence gets his signals mixed when Paige's former fiancé, Matt, returns to the scene.
Ellen and Peter go on a spiritual retreat where he tells her that he feels that she is not has happy as others think, which offends her to a rare point of anger. Meanwhile, Paige thinks Buy the Book is the target of a robbery and she happens to be correct when she, Spence, Joe, and Audrey are all tied up together in the office for the entire weekend by the robber.
Ellen's hard-to-please, grandmother comes for a visit where she assumes Ellen and Joe are a couple, and that Ellen's parents are still together. But after a lifetime of white lies, Ellen and her mother finally decide to come clean with grandma. Meanwhile, Paige treats Spence to a weekend at Caesars Palace in Las Vegas which takes a turn for the worse when he hits his head after falling on the bathroom floor, winds up with amnesia, and spends the rest of the show wondering through the casino thinking that he's a Roman soldier out to protect Julius Caesar.
Ellen tries to speed up her parents divorce by showing them her example of free time in hanging out at a sports bar with Harold, and takes Lois to self-defense classes. But when Lois and Harold begin to have second thoughts after getting stuck in a traffic jam on their way to their lawyer's office, Ellen tries to reason with them, but she inadvertently brings them back together.
At Spence's advice to fill in some of her free time, Ellen volunteers at the hospital where she is assigned to care for an English Patient! When the badly burned man tries to talk to Ellen about his adventures before his accident, he is constantly interrupted by Ellen's recollections of the highlights of her life.
Ellen senses a kindred spirit in herself when she meets an openly gay woman, named Susan, through Richard, an old boyfriend of hers, who enlightens Ellen to her own sexual identity. Confused by this startling self-discovery, Ellen seeks the guidance of yet another therapist and braces herself for yet another moment of truth of her life.
After a discussion with her therapist, Ellen decides to tell the truth about her true repressed sexual orientation to her friends by inviting them over to her apartment to break the news so she can be at peace. Meanwhile, Ellen's hopes for a relationship with Susan are dashed when she tells Ellen that she's not interested, but gives Ellen further confidence to embrace her newfound life.
Ellen decides to tell her parents about her sexuality. But for a person like Ellen, even the best laid plans go airy. While eating out at a Chinese restaurant, Harold and Lois (not surprisingly) don't react well with the news that their daughter is a lesbian prompting Harold to walk out and Lois to ponder this news. Ellen then convinces her mother to attend a gay support group where Lois expresses her feelings about the revelation.
Ellen tries to find out if Ed has a thing against homosexuals after he forces she and Audrey to take down a feminist display at the bookstore. Ellen's suspicions about Ed being a "homophobic" eventually prove correct when he tells her that he doesn't want her around his daughters that she is babysitting. Ellen then quits saying that she doesn't want to work for someone that is prejudice against homosexuals. Meanwhile, Ellen finally moves into her new house and tries to reconcile with Paige who's still shaken by Ellen's "coming out" revelation. Also, Spence asks to ...
While on a double date with Spence, Paige and a dim-witted lesbian friend of Paige's, Ellen runs into her former boyfriend Dan, who's now the owner of the restaurant they are eating at. Dan is taken aback by Ellen's personal revelation to him, but accepts it. But Ellen doesn't know what to think when she still feels herself attracted to him.
Ellen fakes athletic prowess to impress Lisa, her very attractive "spinning" aerobics instructor during aerobics classes she is taking with Spence and Paige. But on a mountain-climbing trip, with Spence in tow, Ellen learns that honesty may have been more effective... and less life threatening.
While shopping with Paige at a local supermarket, Ellen meets two neighborhood women who want to introduce her to their friend who is looking for a roommate. With Spence finally moving out of her house into a place of his own, Ellen agrees to meet with the woman. But due to Audrey and Barrett's interpretation of what "roommate" means, Ellen mistakenly thinks this is a person she is being set up with. Later that evening, Paige, still haven't fully accepted Ellen's new lifestyle, becomes uncomfortable and jealous when the woman, Sherry, arrives and hits it off with ...
Ellen hires a gay plumber from a gay yellow pages phone book she was given to by Peter to fix the plumbing of her house in preparation for a party for the gay social crowd. But the man leaves Ellen with an even bigger leaky sink to remember him by, prompting Ellen to ask her long-term family plumber, Tony, to come to her rescue while dealing with the party guests in the next room.
Ellen meets Laurie Manning, her openly lesbian mortgage broker whom she asks out for coffee. But Ellen later gets confused on where she stands when Laurie brings along a woman friend of hers during an outing at the movies. Meanwhile, Joe opens his new coffee shop, called Cup Of Joe, which he tells Ellen that he had told his uncle that he would name it after him.
Ellen attends her father's annual Civil War re-enactment outing with her father playing General Grant. Ellen wants to play a solder, which brings out hostility from the other men and the sadistic drill instructor, Sgt. Timko, who plans to give her a hard time. Things take a turn when Ellen suspects her father, Harold, is having an affair with Betsy, a field re-enactment nurse, who fixes more than just fake chest wounds.
Ellen faces her toughest challenge when she finally gets to meet Laurie's 12-year-old daughter, Holly, on a movie date who suddenly becomes angry after seeing that Ellen and her mother will only hold hands in private than in public. Also, Laurie finally gets to meet Ellen's eccentric parents, Lois and Harold, at Ellen's house for dinner.
While attending a Hollywood social party with Paige, Ellen spots British actress Emma Thompson making out with another woman and afterward convinces Paige to hire her as Emma's personal assistant while she's in town to film a movie and to receive a Lifetime Achievement Award. Ellen then convinces Emma to "come out," to the public, against Paige's protest. But Emma soon reveals to Ellen that it's not the only sordid secret that she hides of her past. At the banquet, Sean Penn appears with a surprise revelation of his own.
Laurie invites Ellen over at her apartment to spend a romantic night together. So, Laurie sends her daughter, Holly, away and fixes of her apartment nicely which prompts the very nervous Ellen to make a run for it in fear of this new sexual experience and leaving a bewildered Laurie in the cold. Meanwhile, Peter looks after Ellen's parents house while they are away and has trouble with the sensitive alarm system and their barking dog, while Paige, Spence, and Audrey help paint Ellen's new house.
Ellen gets another job as an assistant to a radio talk show host, named Chuck, who repeatedly makes passes at her. When Ellen rebukes the obnoxious Chuck's advances, he leaves in a huff and Ellen is stuck alone and on-the-air at the station for the entire rainy day with nothing but her irrevocable wit, and a Janis Joplin record.
Ellen and Laurie go out to spend their one-month anniversary together where complications arise when Laurie misinterprets Ellen's gift as a sign of moving in together, where as Ellen is not prepared to move that fast. Meanwhile, Ellen's father, Harold, tries to get more closer to Laurie's daughter, Holly, by taking her out to his miniature train shop.