This paper delves into the employment aspirations and struggles for upward social mobility of middle‐class Muslim female youth in Delhi, located in segregated and non‐segregated areas. The paper contends that women respondents navigate constraints such that their class, gender and religious background have an ambivalent role in the production of aspirations but a more definitive one in their realisation. This argument is anchored in the three key themes addressed in the paper. For women from middle and lower sections of the middle‐class the presence of high aspirations does not translate into gainful employment, leading to the problem of fraying hope and ‘frustrated freedom’. They are engaged in prolonged waiting experiencing what Ghassan Hage would call ‘stuckedness’. The upper stratum placed strategically in the Bourdieusian field, can leverage their economic and cultural capital to offset uncertainties around employment and marriage. The third section navigates religious, gender and class‐based constraints by participating in self‐employment activities in a segregated neighbourhood in Delhi. For these women, the segregated neighbourhood has a dual role as an enabler and a barrier to their aspirations.