Abstract: The present invention provides a system for transacting the sale of second-hand items by, in part, using a matching engine for presenting a product to a user in accordance with at least one user attribute and at least one product attribute related to the at least one product, providing a transaction manager for accepting funds from the user in exchange for the at least one product, which funds may be stored in a trust account. User attributes may also be associated with a size gauge where at least one image of the user and the size gauge may be presented to the matching engine. The system may also present a product based on social media interaction between the user and the seller of the product.