[Answer] Before becoming famous, Oprah Winfrey once dated which fellow Chicagoan?

We have looked all around the web to find the most relevant answer to your query: 

Before becoming famous, Oprah Winfrey once dated which fellow Chicagoan?

• Roger Ebert:Early in her career, Oprah Winfrey dated film critic Roger Ebert, and although their romance never blossomed, something great did come out of the pairing. On her show, Oprah revealed that Roger Ebert was the person who persuaded her to go into syndication...while they were on a date! Naturally, Roger took Oprah to a movie on their first date and then treated her to dinner at Hamburger Hamlet. At dinner Ebert calculated on a napkin how much money Oprah could make by syndicating her local talk show. He slid the napkin across the table to show Oprah the final tally and she said, "Deal done!"

If you want to answer this question or elaborate it, just do it with below below format in comment box:

@Answer@YourDisplayName@ 

We will ensure your response will help others.