This study investigates the social, psychological, and cultural dimensions of motivation involved in learning English as a second language in Kuwait. It focuses on students’ experience of motivation, emotions, and their cultural background in search of differences and similarities presented by gender, type of high school, and year in university. The effects of motivation and learning experiences are discussed through using the perpectives of Gardner’s socio-educational model, whereas the influence of learners’ cultural context in second language learning is discussed through using Hofstede’s cultural model. Data were gathered by surveying undergraduate students from a private university in Kuwait, which yielded 233 completed questionnaires. The study employed quantitative methods using SPSS application for descriptive data analysis, correlation analysis, t-tests, and ANOVA. The descriptive statistics were calculated based on the data submitted by the students’ responses. The results revealed significant levels of integrative and instrumental motivation, emphasized by female students, which could be attributed to Hofstede's cultural dimensions of certainty, femininity, and collectivist society. Significant levels were also reported for English classes and English use anxiety, which may be attributed to Hofstede’s power distance, which accounts for the high respect accorded to teachers and teaching. Collectively, the results gained from this study provide guidance to disentangle the multitude of factors that affect English language learners. The findings reported in this study may help instructors who need to understand how learners’ cultural values influence the nature of instruction and point toward future research in analyzing multiple factors that assist language learning.