The Battle of Shaker Heights (2003)

Kathleen Quinlan plays artist Eve
Amy Smart plays artist Tabby

The Battle of Shaker Heights on IMDB

The plot revolves around Kelly Ernswiler (Shia LaBeouf), a young war reenactment enthusiast, who works at his local store with love interest Sarah (Shiri Appleby) and his friend, Bart Bowland (Elden Henson) as they use military strategy against a high school bully (Billy Kay). Kelly's father Abe (William Sadler) works with drug addicts, being clean himself for over 5 years, which is scorned by an angry Kelly, who, when told this, replies, "So what? I've been clean the whole time." His mother Eve (Kathleen Quinlan) is a commercial artist who works out of their garage, who is desperate for Kelly to forgive his father. When confronted as to when he is going to forgive him, Kelly replies, "I'll forgive him when I can go to college. But I can't, can I, because he used all my college fund to buy Mexican Black Tar." Kelly is furious at his father for the torture he put him through.
At the same time, Kelly attempts to woo Bart's older sister Tabby (Amy Smart), even though she's set to get married to Miner, a handsome businessman. Kelly becomes a regular at Bart's house, being over for dinner often, and he impresses Bart's father Harrison (Ray Wise) with their common fondness for war memorabilia, and Bart's mother by complimenting her on her flowers, and he often talks to Tabby in her workshop, pretending to know about painting in order to impress her after bluffing his way through conversation they had in an art store where he was collecting supplies for his mother.
During this time, Sarah asks him to go to an Aerosmith concert, which she has a spare ticket for, telling him it would be good for him to get out more. When he bluntly makes it clear that he knows it would be a date, he tells her he is seeing someone else, obviously meaning Tabby.
Before Kelly and Bart perform their plan for humiliation of the bully, Bart makes it clear to Kelly that he knows he has "his own agenda", at which Kelly is insulted and angry, and Bart displaces it as "pre-mission nervous energy". They recreate an invasion on the street where the bully lives and drag him out of the house pointing guns at him and shouting at him with German accents. They videotape the whole thing and he urinates out of fear.
Afterwards the boys are drinking whiskey at Bart's house and Bart passes out in a chair by the fire. Kelly makes to go home and goes to the workshop to say goodbye to Tabby. He walks in on her crying, as she now thinks the marriage will be off and goes to comfort her, and they kiss.
As Kelly is leaving, Bart sees him and is furious as he knew he was in the workshop. The next day, as Kelly is on a set for a war programme that Bart got them in, Bart hasn't turned up. Kelly is cast in a role to be a jeep driver and when his cue is called, Bart turns up out of the bushes and confronts him about Tabby. Kelly denies it at first and then becomes speechless. As he is about to drive for his cue, Bart attacks him in the jeep and they make a mess of the set.
The next day, Abe is taken into care again for relapsing and Kelly is emotionless. He goes to the wedding the same day, only to have an annoyed Bart tell him that he can't let him in. He sneaks into Tabby's limo before it pulls in and he talks to her, and it is a moment in which he finally realises he must grow up. He gets out of the car and everyone at the wedding sees him and are all confused. He goes round the back of the church to get his bike and leave and meets Minor again, who has no idea of what happened with Kelly and Tabby, and is civil towards him.
Kelly cycles to the clinic where his father is staying and is surprised. They begin to watch television and his mother walks in and is surprised and happy to see Kelly.
In the ending scenes, it shows the voicemail message where Kelly apologises to the Bowlands for his behaviour and asks Bart if he will meet him where he will be selling all his old memorabilia, and gives a hat Bart acquired for him back. He is shown walking down the street with Sarah and they hold hands. Kellys sees the bully again on his lawn where they faked the invasion, and goes over to him and confesses, only to be punched in the jaw. The film ends with Kelly lying on the lawn, holding his bruised jaw saying,"I deserved it".
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