Alex Hitchins, played by Will Smith, believes that sometimes all it takes is a little encouragement for men to win over the women of their dreams, and he prides himself on his ability to help them achieve this. His strategy? Just three dates, usually enough to spark love. In a poignant flashback to his college days, we see a younger Alex struggling to fit in; his heart is shattered when the girl he adored is caught kissing another guy. This painful experience leads him to vow never to fall for another woman, which ultimately drives him to establish his secret "date doctor" business.
At the beginning of the story, a woman named Sara, portrayed by Eva Mendes, returns to work from a short vacation, bringing with her news about a scandal involving a man who cheated on an heiress named Allegra Cole. Though Sara is thriving in her career, her personal life is empty, and she is unbothered by her single status.
Hitch's new client is Albert, an overweight man who has developed feelings for Allegra, his financial advisor. Understanding Albert’s genuine feelings, Hitch agrees to help him. He coaches Albert to impress Allegra during their next meeting, where Albert confidently intimates that she should trust her instincts with her money, shocking his boss in the process. As Hitch remains in the background, Albert forms a connection with Allegra.
Meanwhile, after saving Sara from the advances of a predatory man at a bar, Hitch finds himself drawn to her. Their initial interaction is awkward but piques her interest. He calls her the next day to arrange a "jey ski" date that turns out to be a disaster, yet somehow brings them slightly closer.
As Hitch continues to mentor Albert, they prepare for a fashion event where Allegra's friend Maggie will be present. He offers Albert dance lessons, even though Albert struggles to pick it up. Despite the date being quite imperfect—with awkward moments and a camera flash—Allegra seems to enjoy Albert’s company.
A twist occurs when Hitch encounters a potential new client, Vance, who crudely seeks to seduce women. Unimpressed by Vance’s intentions, Hitch walks away, stating that his services are not for men like him.
In the ensuing events, Sara discovers that Allegra was seen out with Albert, and she learns of Hitch’s involvement in the arrangement. This stirs up trouble as Sara’s boss pushes her to uncover details about the blossoming romance. During a tense dinner with Sara and her boss, Hitch suffers an allergic reaction, hampering his attempts to keep his professional life separate from his personal one.
As the story unfolds, a frantic conversation leads Sara to discover the identity of the date doctor—Hitch. Upset by this revelation, she decides to expose him in a scandalous article, incorporating Albert and Allegra in her write-up, which leads to misunderstandings and heartbreak. The truth fractures Hitch's business, and Albert is devastated, believing he was played.
Feeling betrayed, Hitch struggles with the fallout, deciding to stop believing in love itself. However, after a heart-to-heart with Albert, he realizes he has the power to amend the situation. With renewed motivation, Hitch rushes to reunite Albert with Allegra, ultimately restoring their relationship.
In a parallel story thread, Hitch attempts to confess his feelings for Sara but stumbles over his words. A misunderstanding almost leads to her leaving with what he assumes is a romantic interest, but is just her brother-in-law. After a dramatic confrontation, they reconcile, leading to a heartwarming reunion.
In the film's final moments, love triumphs as we see Albert and Allegra happily celebrating their wedding, proving that with the right guidance and a little encouragement, love can indeed flourish.
