This paper explores the role of cross-linguistic similarity and contextual cues in helping adults learning a second language (L2) to learn idioms. Idioms are expressions that often present challenges to L2 learners due to their non-literal and obvious meanings. This study examined how similarities between idioms in learners’ first language (L1) and L2, as well as the richness of contextual information, affect comprehension and memorization of idiomatic phrases. The results suggest that idioms with structural or semantic similarities to the learner’s L1 are easier to learn, and that contextual cues can significantly enhance comprehension, especially for unfamiliar or dissimilar idioms. These findings emphasize the importance of using cross-linguistic connections and meaningful contexts to improve idiomaticity in second language acquisition. This paper demonstrates the advantages that context and cross-linguistic similarity bring to learning, while also pointing out the limitations of the disadvantages that exist for learning idioms. The two are combined with each other to complement each other to achieve better learning outcomes. Implications for teaching practice and idiomatic pedagogy are discussed.