Research from sub-Saharan Africa has shown the heightened likelihood of dropping out of school for students in sexual relationships, particularly girls. However, our knowledge is limited as to whether the risk of school dropout is exacerbated by the exchange of gifts in the relationship as well as students’ poverty level. Drawing on longitudinal survey data from rural Malawi, this study explores these questions, examining differences by gender and poverty level in the association between being in a sexual relationship in which gifts are exchanged and school dropout for adolescents in primary school. Our findings show that for both boys and girls, being in a gifting relationship heightens the risk of school dropout and eliminates the protective advantages of being nonpoor on dropout. However, non-gifting sexual relationships also erase the protective advantage of being nonpoor for girls, but not for boys. These results point to the value of examining poverty–gender interactions to gain a more nuanced understanding of the impact of sexual relationships on adolescent trajectories.