Research on skipped generation has shown that it is a coin of two sides with competing negative and positive implications on the growth and wellbeing of grandparents and grandchildren (Wen, M., Ren, Q., Korinek, K., & Trinh, H. N., Social science research 80:145−155, 2019; Zimmer, Z., & Treleaven, E., Skip-generation household trends in low-and middle-income countries, 2021). Issues relating to health, finance, living arrangements, wellbeing, education, and sexual and reproductive health of skipped generation households (SGHs) have generated mostly negative conversations in research. However, skipped generation households are not only negative; identified positive implications include the provision of parenting to children who would otherwise have grown up without adequate care. The chapter provides a review of some evidence across Africa (Mtshali, M.G., Journal of Comparative Family Studies 46:75−83, 2015; Muruthi, J. R., Dolbin-MacNab, M. L., & Jarrott, S. E., Journal of Applied Gerontology 40:1280−1287, 2021; Sooryamoorthy, R., & Makhoba, M., Journal of Comparative Family Studies 47:309−321, 2016) and zeroes in on the broad opportunities and challenges that skipped generation households have, and their implications for the main actors with reference to Nigerian societies.