Although the ventromedial frontal lobe (VMF) has been implicated in several complex cognitive tasks such as decision-making and problem solving, the processes for which this region is critical remain unclear. Laboratory studies have largely focused on how the VMF contributes to decision-making when outcomes or options are provided, but in the real world generating appropriate options is likely a crucial and rate-limiting initial step. Here, we determined how VMF damage affected the option generation phase of naturalistic problem solving. A group of patients with VMF damage and two controls groups—age-matched healthy participants and patients with frontal damage sparing VMF—were asked to generate as many options as possible to five scenarios depicting open-ended, real-world problems (e.g., having lunch at a restaurant and forgetting your wallet at home). Both the number of options and the effectiveness of each option generated were examined. Damage to VMF led to a significant reduction in both the number of options produced across all problem-solving scenarios and the ability to generate effective options, most notably for scenarios that were social in nature. We discuss these findings in terms of the mechanisms by which the VMF may contribute to option generation, focusing on proposals suggesting this region is important for integrating subjective value and retrieving schematic representations.