In 1514 he met Chaitanyafor the first time. That meeting changed his life and he decided to leave the service and take up a life of renunciation in the association of Chaitanya and his followers. After visiting Vrindavan Chaitanya had halted at the holy city of Prayaga. It was here that Rupa met him for the second time. At the Dasasvamedha Ghat Chaitanya imparted certain instructions to Rupa Goswami as well as explained the intricacies of the doctrine of Gaudiya Vaishnavism. He was also ordered by Chaitanya to carry out two tasks: to change the position and preserve the lost holy places of Vrindavan as well as to write and preach Gaudiya Vaishnava theology.
On the order of Chaitanya Rupa Goswami came to Puri and resided there for ten months. During the Rath Yatra festival in Puri, he composed one mystical verse that was read to his associates on Chaitanya's request. Everyone present was impressed with his verse. It was proclaimed that Rupa Goswami was the embodiment of Chaitanya's mysterious teachings of rasa. Rupa Goswami due to this reason is considered by Vaishnavas as the foremost follower of Chaitanya. Those who strictly follow his his line of philosophy are known as Rupanugas.
He discovered various holy places that were associated with the amusements of Lord Krishna. The famous deity of Govinda deva was discovered which was installed and worshipped by Krishna's great-grandson, Maharaja Vajranabha.
He died in 1564 CE and his samadhi is located in the courtyard of the Radha-Damodara temple in Vrindavana. In Gaudiya Vaishnava theology, Rupa Goswami is considered to be the incarnation of Rupa Manjari, the foremost junior cowherd damsel who eternally serves Radha-Krishna under the guidance of Lalita (gopi).
Literary Contributions of Rupa Goswami:
Rupa Goswami wrote several texts in Sanskrit on philosophy, poetics, drama and dramaturgy. His most well-known works:
Bhakti-rasamrta-sindhu (The Ocean of Nectar of Divine Love): Bhakti-rasamarta-sindhu is one of the most important books in Gaudiya Vaishnavism. He elaborately describes the traditions of Bhakti from its lowest stage of sraddha up to the highest stage of maha bhava
Ujjvala Nilamani: Ujjvala nilamani exclusively explains the conception of madhurya-rasa. Ujjvala nilamani is considered to be a sequel to the Bhakti-rasamrta-sindhu.
Laghu bhagavatamrta: This is a summary of Sanatana Goswami's book Brhat-bhagavatamrta. It explains the intrinsic nature of Krishna and his incarnations and deal entirely with the devotees of Krishna.
Vidagdhamadhava (1524) & Lalitamadhava (1529): The two works were planned to be written in a different manner. Finally it was completed as two separate plays in Vikram Samvat and Saka era respectively. It is believed that Rupa had a vision of Satyabhama, one of the queens of Krishna in Dwaraka, who asked him to divide the book into two separate dramas. Lalitamadhava deals with Krishna's pastimes in Dwaraka and Vidagdhamadhava speaks of Krishna's pastimes in Vrindavan.
Stavamala: This includes short works by Rupa Goswami.
Danakelikaumudi (1549): This is a one-act play that was written by Rupa in Saka era and narrates the danakeli between Krishna and the Gopis of Vrindavan.
Sri Radha-krsna-ganoddesa-dipika (1550): Here Radha's associates are listed and their characteristics are described.
Mathura-mahatmya: Mathura-mahatmya tells the glories of Mathura. It is in the form of a conversation between Varaha and the Earth Goddess.
Uddhava-sandesa: Here the story from the Bhagavata Purana of Krishna requesting his friend Uddhava to go to Vrindavan is narrated.
Hamsa-dutam: This is a story of how Lalita, the confident of Radha, sends a messenger in the form of a swan to Lord Krishna in Dwaraka.
Sri Krsna-janma-tithi-vidhi: This is a paddhati that explains the process of worshiping the deity of Krishna during the festival of Janmashtami.
Nataka chandrika: This describes the rules of Gaudiya Vaishnava dramaturgy.
Upadesamrta: This is a work that consists of eleven verses which gives instructions to aspirants on the path of devotion to Krishna.