The current study examined 1316 South Asian youth socialized in progressively Westernized contexts: “traditional” Indian homeland single-sex schools, “transitional” Indian homeland co-educational schools, and the immigrant “diaspora” in Canadian schools. Results showed youth in the three contexts were similar on romantic desire. Yet those in increasingly Westernized contexts reported more romantic activities and greater perceived autonomy from parents in partner choice. They were also more likely to consume Western and social media, and possess friends fostering permissive expectations, greater cross-sex network composition, and intimate communication. Involvement with the global media and friends explained the link between the cultural spectrum and romantic experiences. Implications of global restructuring on romantic experiences, media usage, and friendships are discussed, in consideration of gender.