A method for aiding a user in recalling and generating a password. Many times it is easier for a user to remember a place, phrase, person, or other piece of information based on a certain context. The present invention allows for generating a password based on contextual information provided by the user. By providing a context type and a pass phrase, a secure password can be generated. The invention also provides a mechanism for “fuzzy matching”, in which a user only needs to provide a password that is close enough to a stored password to gain access to a website or service. The context type and pass phrase can be used to create a list of passwords (the list being limited to a certain number of entries), each matched against a database of passwords to validate entry.