Ranbir Raj (Ranbir Kapoor), a free spirited idealist – dreamer, arrives in a dreamy surreal town and joins as a lead singer in its swankiest club. Here he bumps into Gulabji (Rani Mukerji), a prostitute, who immediately falls for his naivety and innocent charm. One night he notices a mysterious girl standing alone on a bridge holding an umbrella. As he tries to strike a conversation, she shies away. But he still keeps following her and both end up becoming friends. This mystery girl, Sakina (Sonam Kapoor) forever carries a sadness in her eyes which leaves Ranbir intrigued. But so mesmerized he is with her that his every minute goes into discussing her with his land lady, Lillipop (Zohra Sehgal) and Gulabji.