I find that if students class place themselves in a time period history becomes more relevant for them. I try to make history as "real" as possible and one way of doing that is having your students strike up a "conversation" with a person from the past. With this assignment I have my students interview Franklin D. Roosevelt and ask questions pertaining to him as a President, politician, American living in the early 20th century, person, etc. etc.
Students will need to come up with a list of questions that are factual. Not only will they have to write up questions, but they also will need to explain why they asked these questions. For example, a student may ask "Did having a disability discourage you as a young man to pursue politics?" Their explanation may be "Citizen's might want to know the trials and tribulations our President faced. It also humanizes him as a person in the publics eye."