Mary Horowitz (Sandra Bullock) is a crossword puzzle writer for a Sacramento, California newspaper. As brilliant as her puzzles are, her life is not—she’s socially awkward, lives with her parents, and her only friend is her hamster Carol. After a talk at a school career day where the children make fun of her obsession with words and her red patent leather go-go boots, Mary drags home to face a blind date that her parents set up with Steve Mueller (Bradley Cooper), a cameraman for a cable news channel. Contrary to her belief that he’s probably gay Steve turns out to be handsome and charming, and Mary is immediately smitten. When they go out to his car she attempts to pounce on him but is thwarted by the seat belt; eventually she succeeds. Steve is excited at first, but quickly finds Mary's incessant talking about random facts and their destiny to be together very scary. He is saved by a phone call from work, which takes him out of Mary's clutches. He says he has to go, and that life on the road is tough. He wishes she could join him, but since she has an important job it just won't work out. He gives her an umbrella as a gift and escorts her out of his car before taking off into the night.
Mary misreads his intentions and falls head over heels in love, staying up all night to create a new crossword for the week that’s completely Steve-themed. The whole city is perplexed by the oddball crossword, and Mary loses her job for being unprofessional. Sitting in the bathtub wallowing in her misery, she realizes that she just needed to line up the clues to figure out her next step. She now has no job that would keep her from following Steve on the road. So she starts watching the news and figures out how to track him down. Her first attempt fails--her annoying fact spewing on a bus gets her kicked off in the middle of nowhere--but in the process she charms a truck driver who finds her annoying yet oddly sweet and genuine.
Meanwhile Steve has given no more thought to Mary, consumed with working with over-the-top ambitious reporter Hartman Hughes (Thomas Haden Church) and Angus Tran (Ken Jeong), a fellow journalist and "chaperone." While covering a breaking news story about a 3-legged baby caught in a custody battle, Mary arrives via taxi and finds Steve, who's shocked and a bit frightened that Mary has found him. He'd heard about the crossword "All About Steve," and was naturally creeped out. Steve tells her he has to go to work, and Mary finds herself with some of the odd protesters making signs and lighting candles. Even though they are all a little "off" by normal standards, they're kind and welcoming to Mary, who fits in. She makes friends quickly. Hartman encourages Mary to continue to pursue Steve, and no matter how many times Steve tells her that he doesn't want her there Mary doesn’t believe him. When the story wraps and Steve, Hartman and Angus are leaving the scene, Mary chases after the van in hopes of finding out where Steve is going next. Hartman tips her off that they are going to Galveston to track a hurricane, and accompanied by two of her new friends Mary heads to Texas.
Before they can find Steve, however, a tornado stops them in their tracks and the three friends have to take cover in a sewer drain. Their car is ripped away, leaving them alive but completely alone and deserted. Hartman writes a message on the back of a bucket of fried chicken with their next destination, and Mary decides that she's on a road that she can't turn back on. She has to see where this road to Steve ends. Her friends stick by her and the three of them continue to follow Steve.
The movie culminates at the site of an abandoned mine shaft, where a bunch of deaf children have fallen after the ground caves in on them. News crews from all across the country come in to cover the story, and Hartmann sees this as his chance to beat his competitor and win a shot as an anchor as CCN. One by one the children are pulled out of the mineshaft, and as the last child is pulled out, the ground gives way and the crane tips over. The fire department tells everyone that the ground isn't safe and they all need to move back. Just then Mary arrives and, seeing Steve, races over to see him, falling right into the mineshaft. Suddenly Mary is a media star, and footage of her falling into the shaft is played over and over. The reporters dig up every detail of her life, bombard her parents' home, and CCN puts Steve on the spot to talk about his grief over "his girlfriend." Steve, feeling guilty for how he's treated Mary, goes on the air and says that Mary is perfect the way she is, though most people don't get her. She's kind and smart and she doesn't deserve any of this. Meanwhile, a crowd of Mary's friends gather around the site to hold a vigil. One of her friends confronts Hartman, telling him that he did all of this to Mary, and what she did was bring together a group of wonderful people who actually care about her.
While Mary is fishing her way out of the murky waters at the bottom of the mineshaft, she discovers one little deaf girl that the fire department forgot. Mary, who knows a little sign language, is able to communicate with the girl. As the hours go by Mary at once tries to figure out how to escape the mine and realizes that her pursuit of Steve is futile. She is able to jerry-rig the collapsed crane with counterweights to lift them out, but as they are rising a guilt-stricken Hartman dives into the shaft and brings them to the bottom again. After asking Hartman’s weight, Mary adjusts the rocks and all rise to the surface to be greeted by her family and new friends. Steve apologizes to Mary for his treatment of her, which she accepts before leaving him to join her “normal” crowd.
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