A system and method are provided for a user to check-in to one or more commercial venues according to various check-in options including private, public, anonymous, and non-anonymous check-ins, and for merchants to provide one or more targeted offers to the user based on contextual data associated with the user. In one embodiment, one or more queries may be generated for the user to select at least one of a pubic check-in option, a private check-in option, an anonymous check-in option, a non-anonymous check-in option, or a combination thereof. The system may be configured to determine one or more offers configured for a merchant to be provided to the user based on the contextual data associated with the user.