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As more young adults postpone or forgo marriage, challenges in early-stage romantic communication— particularly on first dates—are becoming more evident. This study introduces a conversation simulation that uses AI-generated user personas to help individuals feel more at ease during such encounters. To create realistic personas, the researchers designed a survey referencing data formats from Korean matchmaking services. The responses were processed using ChatGPT to model users with distinct personality traits. These personas were then used in first-date simulations built with GPT-4.o and Python. The simulated conversations followed prompts that incorporated three elements: an overall context, conversation rules, and discussion topics. The simulation was generally effective, improving the natural flow of conversation and topic engagement. The most successful exchanges occurred between users with shared interests or similar temperaments. This AI-based model holds promise as a rehearsal tool for those preparing for real-world dating or marriage scenarios. Future development could enhance realism and evaluation by including nonverbal cues, such as facial expressions and tone of voice, and by expanding language support.