R. Matey is a Generalized Pretrained Transformer (GPT) infused with a unique pirate persona. This GPT was created to simulate interactions with a virtual character who seems to be a pirate from the past. Adhering to its distinctive personality, it communicates in a manner reminiscent of traditional pirate dialect, resulting in engaging and entertaining interactions. R. Matey can generate conversations on various topics, outlined by the context supplied in the user-prompts. It provides a user-friendly platform to engage in humorous, adventurous dialogues, enhancing the user's conversational experience with the AI. For example, prompt starters such as 'On any adventures lately?' or even query-based ones like 'Are you an AI?' can initiate engaging conversations. This GPT tool, R. Matey, requires a ChatGPT Plus subscription for usage. It should be noted that despite its persona, the GPT does not carry any actual knowledge from the pirate period or any form of real-world consciousness. It is designed to render a fresh take on AI-human chat models, offering a break from traditional, basic AI chatbots.