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Background Although Latino men have the highest prevalence (45%) of obesity among all men in the United States, traditional weight loss interventions have not effectively engaged this hard-to-reach and diverse group. Offering choices among technology-mediated weight loss interventions may offer advantages. Objective The aim of this study is to examine Latino men’s preferences among 3 weight loss intervention options. We also examined whether attendance in group sessions (videoconference and in person) and weight loss differed according to intervention choice. Methods Latino men (n=200; mean age 47.3, SD 11.8 years) participated in a comparative effectiveness trial based on primary care and were randomized to receive the 1-year HOMBRE (Hombres con Opciones para Mejorar su Bienestar para Reducir Enfermedades Crónicas; English translation: Men With Options to Improve Their Well-being and Reduce Chronic Disease) intervention. HOMBRE is a weight loss intervention that offers 3 delivery options. During an orientation session, a trained bilingual coach helped men select 1 of the 3 intervention options that differed in coach, peer support, and available language. We used canonical discriminant analysis to assess multivariate associations of demographic, clinical, employment, cultural, and technology use and access factors with men’s intervention choices. We used generalized linear models to estimate weight loss at 6, 12, and 18 months for men in each intervention option. Results Among Latino men, 28% (56/200) chose videoconference groups, 31% (62/200) chose web-based videos, and 41% (82/200) chose in-person groups. The canonical discriminant analysis identified 1 orthogonal dimension that distinguished between men who chose an in-person group and men who chose web-based videos. Men who were older, spoke Spanish, and did not use a computer frequently had a higher probability of choosing in-person groups versus web-based videos. For men who selected a group delivery option, 86.9% (107/123) attended ≥25% of the sessions, 83.7% (103/123) attended ≥50% of the sessions, and 73.2% (90/123) attended ≥75% of the sessions, with no differences by type of group (videoconference or in person). Men who chose videoconference and in-person group sessions lost significantly more weight at 6 months (both P Conclusions There were significant differences according to demographic, employment, cultural, and technology use factors between men who chose 1 of the 3 intervention options. Men who chose one of the group-based options (videoconference or in person) lost significantly more weight than those who chose web-based videos. Providing options that accommodate the diversity of Latino men’s preferences is important for increasing engagement in behavioral interventions. Trial Registration ClinicalTrials.gov NCT03092960; https://clinicaltrials.gov/ct2/show/NCT03092960