The story starts at Kumbakonam. Arya as Baskaran (a) Boss is the lead character of the movie, who is leading a cheerful life with family and friends and struggles a lot to clear his arrear papers. Santhanam (Nallathambi) is the friend of Baskaran and runs a saloon in Kumbakonam. Saravanan (Subbu Panchu) is the brother of Arya and Chandrika (Nayantara) is a trainee professor.
Boss happens to meet Nayantara and falls in love immediately. Arya tries a lot to impress her and accidentally Arya gets himself caught by Nayantara during his attempt to copy in an examination. As the story progresses Chandrika's sister marries Boss's brother Saravanan. Whenever Boss tries to woo her or proposes to her, he is being Chandrika accuses Boss for his irresponsible behaviors.
In order to marry Chandrika, Boss makes up his mind to earn money and seeks ideas and help from his close associate Nallathambi. They both try a lot of strategies, but nothing goes well. At last Boss and Nallathambi plans to start a tutorial college and acquires loan from Velpandi who gives money to them after laying a difficult condition to them. Somehow Nallathambi and Boss emerge successful in their final attempt.Arya successfully gets his sister married and dreams of marrying his love Chandrika. Boss's dreams shatters when Chandrika's
father rejects his proposal. Later the guest appearance is given by Jeeva as an NRI guy, who has been arranged by Chandrika's father to marry her. It looks like as if the characters for Arya and Jeeva are swapped in Boss Engira Baskaran.
