The first season focuses on the life of Jack Malloy, who has just separated from his wife of 16 years, Jennifer. Ross gives him a stuffed bunny, Mr. Floppy, to keep him company. Unfortunately for Jack, Mr. Floppy starts to talk to him.
It's been two weeks since Jennifer kicked Jack out of the house, and Ryan only just notices. He's just rented an apartment for himself and Jennifer gives him his pillow, blue quilt, a fork, a knife, and his orange juice glass to take with him. Ross gives him his stuffed bunny, Mr. Floppy. He takes Mr. Floppy to his apartment, and he's so screwed up that Mr. Floppy starts to talk to him. Ryan and Tiffany learn to take advantage of being products of a broken home at school. Jack steals back his high school leather jacket from Jennifer while she is out on a date. She comes over to his apartment because she can't sleep with out him next to her, and they end up having sex.
After failing to get one of the three VCRs (even the one that requires you to continuously press the "play" button) from Jennifer in the divorce, Jack sells his car to an old lady and buys himself a new one. Mr. Floppy gets excited because they can watch porno (Natural Born Hooters). Jennifer gets upset because it's their first marriage anniversary after the break up, and Jack forgets what day it is. Jennifer invites Jack over for dinner and cons him into feeling that they ought to exchange gifts, and he gives her the new VCR, while she gives him the crappy one. Mr. Floppy gets mad at Jack for giving away the new VCR, and Jack makes the mop and pizza box talk to demonstrate that he doesn't need Mr. Floppy.
Mr. Floppy thinks that Jack should start dating. While Jack, Jennifer, Ryan, and Tiffany go to Howe High's back to school night, Jack tries to send out "the vibe" to the women there. Amazingly he gets a date with Miss Taylor (Ryan's Civics Teacher), whom all the male teachers and students, and half the female teachers are after. Jennifer agrees to lend Jack the car for the date, but is less than supportive of him. When Jack comes to pick up the car, Jennifer and the car aren't there-- she and Maureen have taken it to the otherside of the block. Jack ends up meeting Miss Taylor 3 hours late, and Ryan's friend the paperboy ends up going home with her.
In order to become more successful at attracting a new man, Jennifer wants Jack to buy her new breasts. When he refuses, she tries to sell her engagement ring and finds out it is glass and 14 karat goldette, and becomes upset. Jack, against the wishes of Mr. Floppy, decides to sell his autographed baseball in order to buy her a new ring. Jennifer tells him that the ball was really autographed by her mother. Jack and Jennifer have sex at the end of the episode.
Since Jack's boss (Jennifer's father) won't give him a car, he decides to buy a moped. Jennifer finally convinces her mother, who came six weeks ago for a two week visit, to go home. As Maureen walks out the door, Jack runs into her with the moped, which of course causes her to continue staying with Jennifer. Jennifer decides that in order to prevent Maureen from suing Jack and getting all of Jennifer's stuff, that Jack should call her "mom" (which he has never done). Features a wonderful daydream medley of scenes where Jack imagines killing Maureen at various stages in his life.
Jennie, Ross, and Ryan are sick in bed with colds, and Tiffany has two days until the Alphi Pi Psi party at the local university, where she plans to mingle with the geeks since "today's big dufus is tomorrow's Bill Gates." Jennifer calls Jack over so that he can pick up food and tampons, and get the car from the mechanic. Mr. Floppy makes Jack to take him along so that he won't be bored in the apartment, and then convinces Jack to escape to Mexico. Jack turns back home after a "conscious attack," gets yelled at for buying the wrong flavor lollipops, and is stopped from running to Mexico again because he ran out of gas in the driveway. Jack and Jennifer have sex in the front seat of the car at the end.
Jennifer is appalled by Jack's, Ryan's, and Ross' table manners, while Jack becomes upset when he learns that Ryan does the dishes and the laundry. Jack encourages him to fight against his emasculation, and Ryan then refuses to do the laundry, so Jennifer kicks him out. Ross is later deposited at Jack's after using the guest soaps in the bathroom. Jack tries to teach the boys how to revel in their maleness, while Jennifer, Tiffany, and Maureen enjoy the silence of a house devoid of belching, and exchange stories about the "gelding of men." For want of food, Jack and the boys raid Jennifer's garbage for left overs and then get food poisoning. After being retrieved from the hospital by the women, the three are made to do the dishes in frilly aprons. Don't miss Tiffany getting hot talking about the riches she will acquire from her man-- "Oh, stocks, diamonds and porkbellies oh my!"
Jennifer wants to get into the Betty Ford Clinic so that she can meet a rich drunk, and tells Jack he'll have to take the kids when she is away for the week. He'll have to pay for her visit or he'll have the kids forever. Jack takes the kids for the night and Ross cuts off Mr. Floppy's foot so that he can have a good luck charm to break his string of bad luck. Ryan steals the foot from Ross, and uses it get a date with Cindy Stalling (whom he dreams of every night). Moments later Tiffany steals it from him, and he promptly loses Cindy, but Tiffany finds a diamond ring in her sandwich. Jennifer gets tips from Maureen on how to fit in at the Clinic. Jennifer takes the foot from the kids and won't give it to Jack because it got her into Betty Ford. Jack unsuccessfully tries to offer Mr. Floppy a new foot from a different stuffed animal, then breaks into Jennifer's house and gets noticed by everyone. Never the less, he steals the foot from Jennifer, and she promptly gets bumped from the Clinic. There's a great scene where Mr. Floppy comes on to a Barbie-type doll that Jack brought home with the rest of the stuffed animals.
Jennifer is depressed because she can't get a date, and wants to be lusted after. When Jack takes the rest of his stuff out her basement, she decides to fix up the house. She hires Matt, a twenty year old who just moved into Jack's building, who was captain of the football, baseball, and basketball teams in high school. When Jack tells Jennifer that Matt has a habit of sleeping with the women he works for, Jennifer goes after him. Tiffany gets really aroused by him, and Jennifer forces her to stay away from him so that she won't have to compete. After Matt shows no interest in her, and runs off with Mrs. Wilson, who has a big butt and four chins, Jennifer complains to Jack that she isn't attractive.
Jennifer goes out with Gavin Drake, "Picture Framer of the Stars," and falls for him because it's the best date she has had so far. Tiffany and Ryan learn that he is a married man at school lunch because he is the father of Chelsea, one of their friends. They tell Jack, and he gets excited because he'll get to crush Jennie by telling her, and it'll be the best thing that has happened to him all year. Mr. Floppy wants him to wait telling her so that he can get gossip about Shannon Doherty out of Gavin. Jack doesn't get to tell her because Gavin asks her to be his mistress. Jeannie seriously considers it, but breaks up with him because it would be too much for her conscience.
Tiffany wants to spend the night at the lake with her friends, including her date Beau. Jack forbids her because he still sees her as a little girl, and does not want her to be taken advantage of. Ryan keeps trying to talk to Jack about his own date, whom he describes as older, an occultist, and criminally insane, but both Jack and Jennifer ignore him. Later, Jack feels about forbidding Tiffany to go, but both Mr. Floppy and Jennifer agree that he made the right decision. Tiffinay then sweet-talks Jack into allowing her to spend the night at the lake. Jennifer gets mad, and they go out in an attempt to retrieve Tiffany.
Jennifer is chaperoning Tiffany's spring dance. Tiffany is in charge of planning the dance, and has invested the funds into war-oriented stocks. Unfortunately, peace breaks out and her investments go bad. Jack has to return his new J. Bean wardrobe (that Mr. Floppy says makes him look like a gay-boy) in order to help fund the dance. Jennifer makes Jack help her with and take her to the dance. Ryan ends up with 10 dates because the girlfriends of the football team want to get even with the team for getting a stripper the week before. The theme of the dance is "The O.J. Trial Under the Stars," and Barry wins Queen of the Prom.
After winning $200,000 playing Monopoly, Ryan thinks he might have a future as a business tycoon and starts to act and dress the part. After Amber's father is mauled by a dog, Jennie is chosen to be the speaker for "Face the Future" day at Ryan and Tiffany's high school. She guilts the kids into going, and tells Jack that he has to go as well. Unfortunately, it conflicts with his weekly basketball game. Jack leaves notes all over his apartment to remind himself to go, but ends up forgetting anyway.
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