Methods of the present inventions allow for private messaging a second recipient of an electronic communication. An exemplary method may comprise the steps of receiving a request to compose an electronic communication from a sender; generating a first electronic communication comprising a first recipient field, a second recipient field, and a first message field; receiving (from the sender) a first recipient electronic address in the first recipient field, a second recipient electronic address in the second recipient field, and a first message in the first message field; and prompting the sender for a private message for transmission only to the second recipient electronic address. Responsive to a negative response from the sender to the prompting step, the method may further comprise transmitting a completed version of the first electronic communication to both the first recipient electronic address and the second recipient electronic address. Responsive to a positive response from the sender to the prompting step, the method may further comprise generating a second electronic communication comprising the first recipient field, the second recipient field, the first message field, and a private message field; receiving (from the sender) a private message in the private message field; transmitting a completed version of the first electronic communication to the first recipient electronic address; and transmitting a completed version of the second electronic communication to the second recipient electronic address.