A successful, wealthy businessman, Wesley Deeds has always done what's expected of him, whether it's assuming the helm of his father's company, tolerating his brother's misbehavior at the office or planning to marry his beautiful but restless fiance, Natalie. But Wesley is jolted out of his predictable routine when he meets Lindsey, a down-on-her-luck single mother who works as a cleaning person in his office building. Outspoken, impulsive and proud, and also recently evicted.