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Henry picks up a new girl every week, giving her an unforgettable fling, only to move on to his next conquest without giving her another thought. Lucy constructs a house of waffles at breakfast every day, and she always thinks its her father's birthday, October 13th; due to brain damage suffered in a car crash, each morning she forgets everyone she met the day before.
Lucy's father is a retired fisherman. Her brother, played in a hilarious tour de force by former Frodo sidekick Sean Astin, is a failed bodybuilder. Every day they labor like slaves to shield Lucy from discovering her condition. Since Hawaii's climate is the same year round, there's no way Lucy will realize what's going on unless someone tells her. Her mother's best friend, the proprietress of the diner where she eats every day, helps shield her from the distressing truth. Every night they paint over the father's workshop, so Lucy can give free rein to her artistic skills on the white walls. And every day is the father's birthday, complete with party hats and Lucy's gift is always the same: a video of Sixth Sense that she bought before the accident, which the two men dutifully watch with her without betraying any hint of knowing the twist revealed at its end.
In contrast Groundhog Day, in which everyone reacts predictably to Phil's manipulations, in this movie what Roth tries one day never seems to work the next. He tries using a toothpick as a door hinge in her house of waffles one day and makes a big hit, but the next day she's all like, "Are you from some country where it's okay to put your hands all over someone else's food?" Roth has to watch his step, because proprieter Nick is only a few steps away and never seems to let go of his meat cleaver.
His hilarious stunts to get acquainted with her are matched only by her hilarious responses. To rebuff one approach, she pretends to speak only native Hawaiian. The next time, Roth pretends he can't read the menu, howling at the counter in tears (really water from his glass) until Lucy comes over to comfort him and "teach him some of the words"; of course, she know all along he was only pretending but was touched that someone would try so hard to pick her up.
Told off by her father, Henry promises to keep away from the diner, but he figures his promise doesn't apply to meeting her other places. Every day he tries a new way of meeting her on the road, asking for a jump or pretending that his stoner buddy is beating him up. It's when he poses as a kidnap victim that Henry is found all tied up in the back of his truck and invited by Lucy's father to visit the house. Lucy is singing at the top of her lungs, having the time of her life painting the workshop. The father reveals that the only times she sings are the days she meets Henry.
Another minor character is Roth's stoner buddy, a native with 5 ever-grinning kids. In a parallel to Lucy's father, he is also devoted to his kids, contstantly delighting them with silly jokes and pranks while encouraging their excellence in activities like golf and swimming. At first, he is Roth's only confidant but one day this all changes.
Lucy sees a sheriff writing her a ticket for expired car registration and storms out of the diner to protest. "It's still October, see? Look at this newspaper!" To her consternation and dismay, the proof she intended to show actually reveals the passage of a shocking length of time. She drives home to ask her dad who is forced to confirm the bad news. Screaming and crying, she is comforted by the three men in her life: her calm, devoted father who hands her a scrapbook with the news article of the accident (the car nearly hit a cow) and a grisly picture of her in the hospital; her ditzy but loyal brother; and her new friend or "boyfriend" Henry.
They drive to the hospital -- a "leading brain clinic" -- where the doctor (Dan Akroyd in a brilliantly understated cameo role) explains her condition. At least it's not as bad as Ten-Second Tom, a man who has no short-term memory at all. Lucy gets a whole day. But in the movie's premise, her brain fails to convert the short-term memories of the day into long-term memory at night.
Henry gets an idea. Instead of trying to shield Lucy from discovering her amnesia, why not make a short film that breaks it to her gently? So the next morning she wakes up to find a videotape marked, "Good Morning, Lucy". She places it into her VCR and we watch with her as her all-time favorite song, "Wouldn't It Be Nice" plays in the background. It's still a shock and she's still very sad to learn about her accident, but at least she doesn't run screaming to the end of the dock and cry for an hour. The home movie ends with Henry's gentle voice inviting her to come downstairs when she's ready, and her father will explain any questions she has.
The biggest question of the movie is how Sandler and Barrymore's characters can really be a couple. Lucy is smart enough to consider this question herself, and after several days of romance ("There's nothing like a first kiss", over and over) she shows up at the seaquarium with startling news. She's been keeping a scrapbook ever since Henry made the home movie (she's no passive object of care, but is her own woman despite her phenomenal mental handicap). Building on Henry's idea of filling her in on the cause of her condition (and a few bits of political news like the fall of Saddam and the rise of Schwarenegger), she has been writing in her diary every night to provide a day-to-day continuity. She comes to realize that she's been holding Henry back from his life's dream of conducting walrus research off the Alaskan coast. So in all fairness to him, she breaks up with him, deleting him from her scrapbook (which she replaces with a computerized Read This document Henry types for her).
Henry completes the work on his boat, and one day he says goodbye to his 3 male friends. But Lucy's father leaves him with stunning news as well as a very interesting present. The news is that Lucy has moved back into the hospital, working as an art therapist for the other memory-loss patients. As Henry sails away from the island, he opens the present: a Beach Boys album containing Lucy's favorite song. As the CD plays Wouldn't It Be Nice, he bursts into tears, cursing Lucy's father as a "sick @#$%#&" for inflicting him with such a heart-rending souvenir of his impossible romance.
Suddenly he has a vivid recollection: Lucy was only happy when (as the Beach Boys sang) they were together:
"No, but come with me. I want to show you something."
In her studio, are dozens of paintings of Henry. Almost every night she's been dreaming of him. He is literally the man of her dreams.
In the final scene, she wakes up to a revised home movie. The update is that she's gotten married! She looks out the window to see icebergs under a clear Alaskan sky, and goes on deck to meet her daughter and husband in the reassuring presence of grandpa.