This paper introduces the \emph{Optimist}, an autonomous system developed to advance automated conjecture generation in graph theory. Leveraging mixed-integer programming (MIP) and heuristic methods, the \emph{Optimist} generates conjectures that both rediscover established theorems and propose novel inequalities. Through a combination of memory-based computation and agent-like adaptability, the \emph{Optimist} iteratively refines its conjectures by integrating new data, enabling a feedback process with minimal human (\emph{or machine}) intervention. Initial experiments reveal the \emph{Optimist}'s potential to uncover foundational results in graph theory, as well as to produce conjectures of interest for future exploration. This work also outlines the \emph{Optimist}'s evolving integration with a counterpart agent, the \emph{Pessimist} (a human \emph{or machine} agent), to establish a dueling system that will drive fully automated graph theory research.