This qualitative study examines the experience of Saudi students in the process of learning English while studying in an anglophone country. Through the lens of progressive educational theory and passive learning style, specific factors such as the students' linguistic background and their current experience were explored. This study sought to uncover how these students perceived learning ESL in Saudi Arabia and how their prior learning has affected their current experience overseas. I examined students' insights through the data collected mainly from semi-structured interviews and discourse analysis. In conclusion, the results revealed two major themes including the unprepared learner in Saudi Arabia and the unprepared learner in Canada. Besides, these students were influenced by the passive style they have received before moving to Canada, and they were introduced to a progressive educational system while studying abroad.