This case study examines the divergent socialization trajectories of two lower-middle-class boys, Utsav and Abinash Tamang, from a remote Nepali village, admitted to a Kathmandu government school in grade 6. Through the lens of socialization theory and personality development, it explores how peer groups, family responses, and self-perception influenced Abinash's dropout at grade 10 and migration to Malaysia as a laborer at age 17, versus Utsav's persistence in schooling. Drawing on Cooley (1902) and Mead (1934), the study highlights anticipatory socialization into deviant subcultures versus reintegrative family socialization, underscoring class and urban-rural dynamics in Nepal's educational context.