Social interactions and conversation skills separate the successful from the rest and the confident from the shy. For college students in particular, the ability to converse can be an outlet for the stress and anxiety experienced on a daily basis along with a foundation for all-important career skills. In light of this, we designed SpeakEasy: a chatbot with some degree of intelligence that provides feedback to the user on their ability to engage in free-form conversations with the chatbot. SpeakEasy attempts to help college students improve their communication skills by engaging in a seven-minute spoken conversation with the user, analyzing the user's responses with metrics designed based on previous psychology and linguistics research, and providing feedback to the user on how they can improve their conversational ability. To simulate natural conversation, SpeakEasy converses with the user on a wide assortment of topics that two people meeting for the first time might discuss: travel, sports, and entertainment. Unlike most other chatbots with the goal of improving conversation skills, SpeakEasy actually records the user speaking, transcribes the audio into tokens, and uses macros-e.g., sequences that calculate the pace of speech, determine if the user has an over-reliance on certain words, and identifies awkward transitions-to evaluate the quality of the conversation. Based on the evaluation, SpeakEasy provides elaborate feedback on how the user can improve their conversations. In turn, SpeakEasy updates its algorithms based on a series of questions that the user responds to regarding SpeakEasy's performance.