In the opening of his radio talk on Indonesian culture broadcasted in Singapore in 1960, Singapore writer Lu Baiye highlighted the close connections between Singapore, Malaya and Indonesia and described them as “brother nations that share the same culture and ethnicity.” Lu Baiye, who demonstrates a literary vision rooted in Southeast Asia, is recognized for contributing to the development of the Malayan identity through his non-fictional essays and the Sino-Malay journal that he edited. Comparatively, his modernist fiction and poems, which were written as “Wei Beihua,” have remained relatively obscured in literary histories. Rather than treating Lu Baiye and Wei Beihua as distinct authorial identities, this paper explores how Lu Baiye’s vision of the transregional connections between Singapore, Malaya and Indonesia could help us understand his modernist works. Specifically, by examining his works through the lens of his sojourn in Indonesia, his interactions with Indonesia’s Angkatan 45 writers and Malayan nationalism during the 1950s, this paper questions: how did his Indonesian experience shape his aesthetic philosophy and spur his nationalist agenda? How do we understand the tensions between the modernist and nationalist impulses in his works? In a broader context, how should we make sense of such transregional literary connections in light of the Cold War and decolonization movements in Southeast Asia? In addition to presenting a more complex picture of Wei Beihua’s literary career, this paper argues for the importance of regional Southeast Asian networks that tend to be overlooked in Sino-centric discussions of Sinophone Southeast Asian literature.