A method may include receiving, at a system of a ticketing marketplace, a request for a ticket to an event from a device of a user; generating a query for the user based on the ticket requested, the query requesting information from the user regarding a user preference associated with the ticket for the event; directing the query to the device of the user; in response to directing the query, receiving a answer from the device of the user; applying the answer to a machine learning model to determine a recommended ticket for the user, the machine learning model generated based on an association between ticket locations at a venue of the event and natural language phrases of users associated with the event; selecting the recommended ticket for the event based on an output by the machine learning model; and automatically facilitating purchase of the recommended ticket.