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Personalized AI assistants, a hallmark of the human-like capabilities of Large Language Models (LLMs), are a challenging application that intertwines multiple problems in LLM research. Despite the growing interest in the development of personalized assistants, the lack of an open-source conversational dataset tailored for personalization remains a significant obstacle for researchers in the field. To address this research gap, we introduce HiCUPID, a new benchmark to probe and unleash the potential of LLMs to deliver personalized responses. Alongside a conversational dataset, HiCUPID provides a Llama-3.2-based automated evaluation model whose assessment closely mirrors human preferences. We release our dataset, evaluation model, and code at https://github.com/12kimih/HiCUPID.