Pregnant adolescents’ diet and eating habits are inadequate; however, their association with gestational weight gain (GWG) is uncertain. We aimed to analyze whether there is an association between dietary and nutrient intake and eating habits with GWG among pregnant adolescents and their offspring’s birth weight. A longitudinal study was performed with 530 participants. We assessed GWG and applied several tools, such as a food frequency questionnaire and 24-h recall, to obtain dietary and nutrient intake and eating habits. The birth weight of adolescents’ offspring was registered. Later, we performed crude and adjusted Poisson models. The mean age was 15.8 ± 1.3 years. Of all food groups, the lowest frequency of adequate intake corresponded to vegetables (7%) and legumes (10.2%). Excessive (36.8%) and insufficient (40.9%) GWG were observed. Pregnant adolescents with inadequate legumes intake increased the probability of excessive GWG: (PR 1.86 95% CI 1.00–3.44). Cereals and grains were positively associated with GWG: (PR 1.65, 95% CI 1.18–2.29). Energy, macronutrient intake, and eating habits were not associated with GWG. Offspring’s small gestational age (SGA) increased when pregnant adolescents had inadequate sugar-sweetened beverages intake: PR (1.58, 95% CI 1.01–2.49) and when pregnant adolescent watched television (TV). In our sample of Mexican adolescents, dietary and nutrient intake and eating habits were inadequate. Excessive dietary intake from cereals, grains, and animal-sourced foods along with insufficient legumes were associated with excessive GWG. Watching TV while adolescents ate was associated with the birth weight of the offspring.