This dissertation consists of three research papers that explore the fluidity and multiplicity in people’s social relationships and early working life by quantitatively analyzing personal experiences through longitudinal data. The first chapter investigates whether and how friends can serve as substitutes for spouses/partners and become “new family” given the rising prevalence of singlehood and kinlessness phenomena in modern populations. Using data from a three-wave panel survey in the UCNets project, which provides extensive information on individuals’ network dynamics and well-being, we address the research question by comparing the versatility of connection’s roles in support provisions, examines the short-term and long-term effects of experiencing formations and dissolutions of spousal relationships on non-kin network dynamics, and testing the impact of spouse-like ties and friendship on individuals’ well-being. Our findings suggest that after spouses/partners, close non-kin ties are the next best providers of social support. However, spouses/partners are irreplaceable for their versatile role and dominant support in individuals' social lives and well-being. We find potential substitutability in women's large close non-kin networks (approximately eight members) compensating for the absent spouses/partners. Transitions from partnership to singlehood are challenging, as dissolution temporarily triggers the addition of one reported close non-kin but reduces network sizes by more than two members in the long run. This study highlights the importance of further research on measuring the resilience of personal networks and calls for greater policy attention towards providing social and institutional support for the elderly in singlehood. The second chapter is an up-to-date portrayal of Asian Americans’ experiences in kinship networks and family bonds. While increasingly mainstream popular cultural products feature Asian Americans as experiencers of emotionally intense relationships in family life, we utilize the UCNets dataset with an unusually large Asian American group and detailed information on individuals’ full social networks to empirically test this generalisation. Using multi-level analysis with tie-level data nested in respondent-level structure, we found an Asian-specific pattern of mother-daughter and potentially father-son co-residence, and more reliance on immediate kin for support during emergencies for Asian Americans than whites. Furthermore, our findings suggest that Asian Americans are inclined to “distancing” in managing their social relationships as they identified fewer connections with “closeness”, especially distant from extended kin among all family members. We challenge some generalized stereotypes on Asian Americans’ family relationship experiences as we found no evidence for network size disadvantages or kin dominance in Asian’s social networks in comparison with other racial/ethnic groups. Also, we don’t find strong reciprocity in support exchange between Asians and their immediate kin as potential signals for burdensome family obligations, nor are Asian Americans particularly vulnerable to emotional tension in their family and social life. This study breaks down the cultural myths of Asian American’s family relationship experiences and provides an in-depth discussion on the emotional tension flowing in interpersonal relationships which is lacked in previous quantitative research on family bonds. Chapter three presents an in-depth investigation on the students’ earning-while-learning (EwL) experiences in the UK. Working alongside schoolwork has been a rising and prevalent behaviors worldwide, yet students have rarely been seen as workers. With the national longitudinal dataset Next Steps which follows a student cohort from age 13 to 25, we investigate the work experiences and life trajectories for youths from early adolescence through early adulthood. We find prevalence of EwL with more than two-thirds of students ever worked while studying before leaving education. We also find that young male students are more likely to work than females before age 16 and the trend reverse afterwards. Early EwL experiences are significantly associated with higher chances of engaging in work-related activities during life trajectories at ages 16 and 18. Contrary to the media criticisms, our findings also suggest a slight positive long-term association between pre-18 EwL experiences and the chances of being a degree-holder at age 25. Moreover, our findings show a modest but significant protection effect of early EwL experiences against young people being in NEET status at age 25. This study calls for positive re-evaluations of EwL from researcher and policy makers, and a new “working-life-course” framework that treats students as part of the work force and their working life experiences as integral and beneficial.