Beautiful Ann has not been married yet however; there is lots of information about her love affairs. She was once in love with founder of music magazine Spin, Bob Guccione, Jr... She also dated Dinesh D'Souza for several years. Dinesh is a political commentator, author and a conservative writer. She was also engaged with him.
In October 2007, Ann was seen with Andrew Stein having romantic love affairs with him. Andrew is a Democratic politician from United States. They dated each other for several months. However, with the start of 2008, they called off their love life citing irreconcilable differences.
Ann completed her high school graduation from New Canaan High School in 1980. She then joined Cornell University and majored in history. She finally earned her Bachelor of Arts degree from there in 1984. After that she attended University of Michigan Law School and she finally earned her J.D. in 1988. While she was in University of Michigan Law School, she also worked as an editor of the Michigan Law Review for several months. She then joined United States Court of Appeals for the Eighth Circuit as a law clerk for Pasco Bowman II. She became specialized in corporate law and then she joined United States Senate Judiciary Committee in 1994.
As a writer, Ann has published 11 books till date. In 1998, she published her first book under the title, High Crimes and Misdemeanors: The Case Against Bill Clinton. Most of her books were listed in New York Times Bestseller list and several of them also spot no 1 in this list. Her net worth is said to be around $8.5 million.