Advancements in multimodal Large Language Models (LLMs), such as OpenAI's GPT-4o, offer significant potential for mediating human interactions across various contexts. However, their use in areas such as persuasion, influence, and recruitment raises ethical and security concerns. To evaluate these models ethically in public influence and persuasion scenarios, we developed a prompting strategy using "Where's Waldo?" images as proxies for complex, crowded gatherings. This approach provides a controlled, replicable environment to assess the model's ability to process intricate visual information, interpret social dynamics, and propose engagement strategies while avoiding privacy concerns. By positioning Waldo as a hypothetical agent tasked with face-to-face mobilization, we analyzed the model's performance in identifying key individuals and formulating mobilization tactics. Our results show that while the model generates vivid descriptions and creative strategies, it cannot accurately identify individuals or reliably assess social dynamics in these scenarios. Nevertheless, this methodology provides a valuable framework for testing and benchmarking the evolving capabilities of multimodal LLMs in social contexts.