Pete, Berg and Sharon, three close friends from college, are introduced, along with their workplace, Beacon Street Pizza.
Berg thinks he may have drugged Pete before an important architecture presentation.
Feeling neglected by Sharon, the guys plan to sabotage her new relationship.
Berg and Sharon set Pete up with a girl they find listed in the personal ads, but she soon makes it clear she won't let anyone come between them, even to come in Berg's bedroom at night with a baseball bat.
Berg gets suspicious of Pete when he always want's to deliver the pizza to 845 Arlington. So Berg makes the delivery for a change and discovers that it's a gorgeous artist who paints with her nude body that's been making the orders. This leads Berg and Sharon to believe that Pete is cheating on Melissa with her.
Pete and Berg reflect on their college days when Bill asks them how come neither of them was ever romantically involved with Sharon.
When Berg notices he's no longer first in his class he goes out to find who is. He finds out it's a beautiful female co-ed, so he tries to get her get drunk so she won't be able to study for the test the next day.
Sharon decides to quit her job but her boss tells her to think it over in Aruba. She decides to bring Pete and Berg along, but problems arise when Pete has a last minute job interview that seems to go on forever. They are then delayed when Sharon must answer questions from reporters at a press conference when her company dumps thirty thousand gallons of toxic waste in Chesapeake Bay. More problems arise for them when Berg has a medical emergency to attend to. They end up missing their flight to Aruba and partying at Beacon Street Pizza.
Pete has a new girlfriend, problem is Berg had a one night stand with her three years ago. He doesn't plan on telling Pete until Pete tells him that their going to spend the night at a Bed & Breakfast. It seems that she got Berg's name tattooed on her ass. Berg sends Sharon into the locker room at her gym to see if the tattoo is still there. It is and now all the women at the gym think she's a lesbian. Berg ends up telling Pete and Pete doesn't care cause he likes her too much.
It's homecoming and Pete and Berg plan to get luxury box seats to the homecoming game to upstage some old college friends. The get them just before the game starts but they're counterfeit so they busted. They escape the security room and get busted again. This time they go to jail. Also Sharon tells her ""friends"" that her boyfriend is a music executive and he thinks she's embarrassed of him cause he's only a jukebox repairman. But then she thinks he's embarrassed of her when she finds out he told his friends she's a stripper.
Pete has to choose an elective course. He chose metallurgy but when Berg brought his course choice card in he changed it for a course in sports broadcasting. At first Pete's mad at Berg but soon learns to enjoy it. Also Sharon tries to prove that her boyfriend isn't dumb.
It seems as though Berg has lost his mind when he goes on a murderous rampage. The victims (1) Tim, (2) Johnny, (3) Mrs. Himmelfarb, (4) Ashley, (5) Cop, (6) the real Berg (by Pete), (7) Sharon and (8) Pete. However, Berg is innocent it's actually an impersonator that turns out to be Mimi from The Drew Carey Show.
When Berg finds out that Ashley went to visit her boyfriend at Oxford he flies all the way to England to be with her. It turns out it is Oxford, Mississippi. Ashley's boyfriend says he'll move to Boston so they can stay together. Pete and Johnny get jobs as limo drivers. Berg and Ashley finally kiss.
Sharon and Johnny want to start a new Thanksgiving tradition and be alone. But plans change when Pete's grandpa comes down unannounced and Berg invites Ashley and her boyfriend Justin. Berg and Pete both hate Justin. Berg and Justin both compete for Ashley's love but she apparently dumps both of them. While trying to break Ashley and Justin up Berg almost ends up breaking up Sharon and Johnny.
Pete enlists the help of a TV love guru to help Berg and Ashley when Berg calls Ashley to tell her that he thinks they shouldn't see each other anymore. She doesn't take very well and breaks down and cries. And for Sharon and Johnny because Sharon is jealous of Johnny's friend Sean when she finds that Sean is a woman.
Pete is put in charge of watching Michael after school which is fine, until he asks Berg to do it for a day. Berg brings Michael to the dog track to help him learn his fractions. Sharon asks Johnny to move in with her.
When Sharon uses an embarrassing underwear ad that Berg had posed for four years prior, for a contest he goes to great lengths to get one of her. Pete realizing he has no parental rights with Michael because he's just the guy dating the mother asks Kaitlyn to marry him. She refuses on the basis that they've only known each other a month and tells him that they should take a break from each other for a while.
When Sharon is up for a new job she learns she never graduated college. When she goes to verify she learns that she hadn't paid her $210 of parking tickets. She had given the money to Pete and Berg so they could go and pay them for her but they had to bail her father out of jail. So she pays the tickets but finds out that the requirements have changed and she needs to retake freshman English. When she puts two and two together she thinks that instead of paying her tickets they had bought a $200 bottle of champagne but later learns the truth, which is that the money she had given them to pay the fines was actually used to bail her father out of jail, after he caused a drunken ruckus due to his recent bankrupcy and the fact that he had just lost his job. The champagne that Pete and berg had was actually a gift from a girl they had never met before
Ashley comes back and tells Berg she dumped Justin to be with him. Berg now has quite a dilemma, choose Ashley the woman he's been chasing for months or Vanita a woman he's just met. He wants to choose Vanita because he thinks he has a better chance with her. So he dumps Ashley but she won't let go she follows him to the restaurant where he has a date with Vanita and ends up breaking them up. Johnny and Sharon get back together.
Berg gives Ashley a key to his and Pete's apartment without telling Pete. Pete doesn't like because he hates Ashley. Ashley doesn't find out that Pete hates her until Sharon tells her. Now Ashley won't talk to Pete, Sharon won't talk to Ashley because Ashley said Sharon has a big mouth. But they all find someone to blame for this, Johnny. You see Pete went to talk to Sharon and Johnny and Sharon got mad at Johnny for mentioning Shawn's name again so she went upstairs and Ashley was there. Sharon told Ashley Pete hates her and when Pete asked who told her that she said that Sharon told her because Sharon has a big mouth. Berg gets the whole thing settled though. Berg becomes a ringside fight doctor but gets fired when he tells the fighter that he should call it quits because he has extreme brain damage.
Pete quits his job at the pizza place and tries his hand at psychiatry. The job doesn't work out but he lands a job as a career counselor after he gets his career counselor a better job. It seems he can get a job but for other people. Ashley and Sharon start hanging out together and reveal secrets about Berg.
Sharon can't seem to give Johnny an answer at first but eventually comes out with ""Yes, in theory"" as it's obvious she's not sure about marrying him but doesn't want to hurt his feelings. Pete flies to Paris to get away from everything and gets hit by a car driven by a beautiful French woman that he later starts dating, even though she can't speak a word of English.
Sharon and Johnny move to the basement because it's cheaper but when Sharon discovers that Johnny has over 23 thousand dollars in the bank she wants to stay. Johnny refuses to go back up because he says that that's his life savings and that he wants to buy a house. Ashley gets a new roommate but Berg scares him away to get even at her for scaring away a nurse he was trying to get a phone number from. Pete is afraid to pick up a package that came in the mail for him because Irene is holding it for him.
Ashley has a New Year's Eve party, and Berg manages to get Robert Goulet to sing at her party after treating him for an ear infection. When Goulet learns that he cannot fly to the destination where he is doing a gig, Berg siezes the opportunity. But he has to work that night, so he swaps with another doctor who Ashley has a crush on, and she thinks he did it intentionally. Johnny tries to get out of a romantic evening with Sharon to hear Robert sing, he says that his dead grandfather used to sit him on his lap when he was a kid and play some of Goulet's songs. Pete invites Irene to the party and she surprises him by acting normal. He even starts to fancy her, but Goulet moves in on his gal before he can get anywhere with her. To be a nice guy, Berg goes back to the hospital and swaps back his shift with the English doctor that Ashley likes. Ashley goes to the hospital to thank him and they end up having sex on a hospital bed.
Sharon and Ashley get drunk and in her drunken stupor Sharon asks Ashley to be one of her bridesmaid's, but regrets it when sober. Pete, Johnny and Berg go to a laundromat/bar and Pete tries to meet a woman but blows it by Johnny's slugs (fake quarters), Johnny uses fake quarters and gets caught and Berg gets his clothes stolen.
Everyone at the hospital is making fun of Berg for his actions at the bachelor auction so he tries to regain their respect by working nonstop until he almost kills a patient accidentally. He's suspended from the hospital for that. Sharon volunteers to read to children at the hospital and Pete becomes a volunteer fireman.
The guys at the firehouse make Pete believe that Marty has a thing for him. Pete, Berg and Sharon decide to hang out at O'Malley's, their old college hangout, just like old times since Johnny is having his bachelor party but Johnny shows up anyway and Berg gets mad at him for ruining their evening and punches Johnny right in the face.
The guys at the firehouse find Pete's make-up bag and the fire chief asks Pete to give his daughter a makeover. In hopes of getting off probation at the hospital Berg lends his apartment to his superior so she can take a nap but she has an affair instead. Sharon has a tea party and Pete and Berg's invites members of the hospital but the wrong ones show up first and they think that she's running a prostitution ring.
Sharon and Johnny get joint checking accounts but Sharon makes all the important choices, Pete is stressed when Marti gets into fireman boot camp before he does and they admit to each other that they like each other, Berg is depressed so he visits his parents only to discover that his mom threw his dad out because he cheated on her.
A bear mauls Pete and he thinks Marti doesn't care for him when she doesn't rush to go see him. Berg and Irene try to keep what they did after the wedding a secret but they end up sleeping together again. Johnny shows Sharon the house he bought for them and it's in serious need of repair. Nomar breaks up with Ashley because of something Pete told him.
Johnny confronts Berg and Berg convinces him not to tell Sharon. Sharon finds out and she tries to use it against Johnny but he keeps his promise to Berg and tells her that it Pete and Ashley that are sleeping together. Nomar is thinking of leaving Boston because of Ashley so an unruly mob sets up outside their apartment building and harass her. Marti convinces Nomar to stay.
Pete tries to locate a woman he saw on the subway, Johnny tries to fix Ashley's bathroom plumbing and he has to turn off the building's water supply, which leaves Berg with a head full of shampoo. A dog follows Sharon home and she has him lick the dishes clean but he accidentally eats her wedding ring. Ashley refuses to give up her seat on the subway to a pregnant woman so four pregnant women hound her.
Pete, Berg and Johnny try to get into a club but end up drinking beer outside a convenience store, after Jonny complains about the price of the beer in there. When they return later to the club with Germ none of them are allowed in, except for Germ. They then go back to to the convenience store but end up getting arrested for drinking in the street. Sharon finds out that Johnny doesn't wear his wedding ring and goes out with Ashley to the club to try and help Ashley find a man, and for Sharon to find Jonny so she can kill him. But they end up having a great time and get piles of phone numbers from single guys.
Pete accidentally cuts the tip of his finger whilst making a salad and trying to apologise to Berg for sleeping with his mother. Berg takes him to hospital via taxi, as he says it will be quicker than ambulance or bus. But when they get out of the taxi, Berg leaves the finger behind and spends most of the day trying to find it. But it turns out that Pete is playing a trick on him, as he wants Berg to accept his apology. Berg accepts the apology thinking that Pete's finger is long gone but Pete had it the whole time. Ashley gives a reluctant Johnny a psychlogical test for a project, and ends up getting some very intresting insights. Meanwhile, Sharon gets a job as the assistant of a crooked lawyer, and only realises when they claim $30,000 for a man who ""lost the use of his legs"". But she keeps the job in attempt to clean his illegal ways
Berg tells Irene that he loves her and she doesn't say it back. Berg takes this to mean that she is no longer intrested in him and ends up going to a comic book convention, where he meets a girl from his high school who was fat and ugly and was also obsessed with him. She believes that it was their destiny to meet, especialy after they meet again at the hospital. Berg starts to think that this girl is better for him than Irene. Pete and Ashley go to the movies, both pretending that they are waiting for dates, but end up having a great time with each other
Pete has a near death experience and he believes that he and Ashley are meant to be together. Ashley has a dream about Pete so she goes to talk to him and they end up sleeping together. Berg wants to see if there can be anything between him and Katie and he discovers that she's been stalking him for eight years. Irene won't take Berg back because now she's seeing her mailman.
A jealous Berg tries to get Irene back but ends up screwing it up again, as he won't leave her alone and keeps on having conflicts with Roger, her new mailman-boyfriend. Pete tries to convince Ashley to stay by spending more time with her and making her a picnic in the park, but he gets stood up becuse Ashley doesn't want to get involved with pete as she's moving, and it will end in heartache when she does leave. Johnny wants to spend more time with Sharon, so he helps Sharon serve a subpoena to a man who has a scary dog, and they spend the day together trying to get through the garden to his letter box