Various systems and methods for a personal messaging assistant system are described herein. A personal messaging assistant system comprises a display; a processor; and a memory, including instructions, which when executed on the processor, cause the processor to perform the operations comprising: receiving an indication to transmit a message from a sender, the message including a recipient and a body; determining a relationship between the sender and the recipient; determining a message context based on the body; determining whether the message context is consistent with the relationship; and presenting on the display, a warning when the message context is not consistent.