Willie Conway (Timothy Hutton) finishes the last few notes of a set at an NYC bar, and counts his tips from a glass on the piano. He takes his change and heads out into the cold winter night to take a Greyhound coach across the border for a High School reunion back where he grew up.
His old twenty-something High School buddies haven't moved on with their lives. Tommy 'Birdman' Rowland (Matt Dillon) and Paul Kirkwood (Michael Rapaport) own a snow-plough business, and hire their friend Kev (Max Perlich) to lend a hand. They each have their issues - Bird, the old High School quarterback, is having an affair with his old High School sweetheart, Darian Smalls (Lauren Holly) ... who happens to be married, and has a daughter. Paul couldn't commit to his ex, Jan (Martha Plimpton), but when she moved on to be with 'Victor the meat-cutter', he is filled with jealousy and blocks her driveway with snow every night.
Michael 'Mo' Morris (Noah Emmerich) is the only old buddy who has matured - he is married with 2 kids, and is content with life it seems.
Mo picks up Willie from the coach station and drops him off home. He has a lonely house since his mom died - leaving behind a heart-broken old man, and Willie's wayward younger brother Bobby (David Arquette). Outside, Willie sees for the first time his young neighbor, Marty (Natalie Portman), making a snowman.
After hanging out with his pals, next day he meets Marty again - who gives him some snow-shovelling advice, which breaks the ice (get it? ok, not that great) in their friendship. She likes his burns.
Paul buys a ring for his ex-girlfriend Jan and proposes. But it's too little, too late. And the diamond has a brown tint to it. she flat refuses, and he is heart-broken.
That night, the old friends meet at a reopened bar in town, managed by Stanley 'Stinky' Womack (a much slimmer Pruitt Taylor Vince). Already Paul argues with Birdman, who doesn't take kindly to his advice, and then the others.
Next day, Marty and Willie meet again. She asks if he has a girlfriend. He tells her that he is seeing somebody - a girl called Tracy. Marty asks if they have plans to get married. Willie has been reluctant to commit, and doesn't want to stick around to hear relationship advice from a 13year old.
Meanwhile, Tommy's girlfriend, Sharon (Mira Sorvino), has had another jealous fight with Tommy (she knows about Darian). She asks her friends for advice. They tell her to ditch him, but instead, as it's his birthday soon, she wants to try one more time and salvage the relationship. They reluctantly agree to help her throw a surprise party.
The old friends, including Mo, are back in the bar again when in walks Stanley's cousin, Andera (Uma Thurman - what a cast!! Who was the casting agent on this one, again?!). The men all fall for her instantly. They down shots, and Willie is asked to play something. After a little warm-up, the boys break into "Sweet Caroline".
Next day, Birdman and Willie are invited to a long, and random, lecture/monologue by Gina (Rosie O'Donnell) about the virtues of real women. Back home, Willie is jealous when he sees that Marty has suddenly got a boyfriend.
Sharon throws the surprise birthday party for Tommy. Things are going great - until Darian shows up, drunk, and makes a move on Tommy. Sharon and her friends leave. Tommy drives Darian home, and she makes a move again but Tommy turns her down. Darian is angry, revealing her true character. Instead Tommy tries to patch things up with Sharon, but it's too late.
Clearing up after the party, Willie opens up to Mo about his feelings for Marty. Mo puts him straight. Willie is having cold-feet about taking things to the next level with his girlfriend. He knows Marty will be stunning in 10 years time, but it's the beer talking.
Willie and Mo head off to the frozen lake the next day with Mo's kids. Willie leaves him to it and joins Paul and Kev in an ice-fishing shack. When he leaves for air, he sees Marty skating with her friends. He goes to say 'hi'. As they talk, he hears that she has finished things with her boyfriend, Andrew, because she has found someone better - Willie. She falls into his arms.
Willie is embarrassed, but a little giddy. Mo almost falls over in shock. Marty asks him to wait for her until she is 18, in 5 years time. But Willie tells her that it would be unfair to wait - she still has a lot of maturing to do and in 5 years will have forgotten about him, while he'll still be waiting. He doesn't want to be the Winnie the Pooh to her Christopher Robbin - as he knows that is how the story ended, when Christopher outgrew Pooh. She skates away.
Paul somehow manages to score a date with Andera. He takes her to a bar - the same one which Jan is at the bar with Victor. Andera, as a favour, flirts with him - but when Paul tries to score a kiss she smacks him and leaves. She walks home alone, turning down an advance from Tommy on the way.
Paul is still upset, and gives Willie a talk about why he prefers models - the promise of a better life. Meanwhile Tommy meets Darian in the library, who asks him to go to the reunion, where things will be like they were before. That night, Willie drowns his sorrows at the bar. He is joined by Andera. After two unsuccessful attempts to leave with him, she gives in and they go to the ice shack.
Andera has a boyfriend. Willie, suddenly forgetting his feelings for Tracy -- and Marty -- says he is jealous. After another unsuccessful attempt, she leaves - and heads home to Chicago the next day.
Tracy arrives from New York. She is a big hit with Willie's old man and Bobby. Willie has feelings for her again. Marty is heart-broken. Willie has kind words for her -- he wants to keep in touch whatever happens, because he knows she will grow up to be an amazing person.
The guys have a pre-reunion party at Mo's. Tommy has decided to do the right thing and avoid Darian - and miss the reunion. Instead he heads down to the bar - and bumps into Steve, Darian's husband, and his frat buddies.
Meanwhile Darian is at the reunion, alone. She is confronted by a man who had/has a weight problem, and says that although she was something to look at, she was as mean as a snake.
After he refuses to be bought a drink, suddenly Steve opens up and tells him he knows about what has happened with his wife. They are going to settle it outside - Tommy doesn't believe Steve to be a man to fight his own battles. After a little insult he leaves ... and is followed by the four men. He gets in a few good punches, but is smacked over the head with a rock and then held while each man gets a free punch, and then kicked while he lies on the ground.
He is found by the barman, who phones Mo. The boys race over to the bar to find a badly-beaten Tommy. Immediately they get back into the truck and head over to Steve's house. Steve calls his friends. Mo threatens Steve -- his friends show, but Willie thinks quickly and rams the frat boys' car into some snow. Mo is about to beat Steve when his little daughter shows up and asks what is wrong. Mo can't do it and leaves. As they leave, Darian drives towards the house to deal with the mess she has made.
Tommy is taken to hospital where he need stitches and has a few broken ribs, but generally is ok. Sharon stops round and takes pity on him. That night, Paul, overcome with emotion, and having learnt that Jan and Victor are engaged, decides to clear her driveway from snow, for a change, as an act of kindness.
The next day Willie stops round to check on Tommy and to say goodbye as he has decided to leave and head back to NY with Tracy. Sharon has stayed with Tommy overnight. Willie tells Tommy not to mess it up this time. Tommy is still a little reluctant to visit - he'll never leave the town.
Willie and Tracy pack the car with luggage. Willie introduces Tracy to Marty, then says goodbye to Marty one last time and gives her a kiss on the cheek. Paul shows up to wave them off. Paul recognises Marty as "the little neighborhood Lolita", she has a few words for the-good-for-nothing High School buddy as well. Paul tells Willie not to forget about them, even though "nothing changes in the Ridge but the seasons!"
As they pull away they run past Kev, who tells them to 'be cool forever', and then out of town to "Sweet Caroline".