Oprah Winfrey's Loves & Hookups

Who is Oprah Winfrey dating? Who Oprah Winfrey dated; list of Oprah Winfrey loves, ex boyfriends; breakup rumors. The loves and relationships of Oprah Winfrey, listed by most recent. While it's maybe a little scandalous that gal pal Gayle King isn't on the list, more shocking still would be if she were added to the list amidst the discovery of an Oprah starring celeb sex tape. Not that the multi-media mogul would ever allow a celebrity sex tape to surface (if it were ever to exist), but what a trip to think of Oprah co-mingling with the likes of Tommy Lee on the list of celebrities with sex tapes .

  • Stedman Graham
    Photo: Metaweb / CC-BY

    Oprah Winfrey and Stedman Graham's relationship dates back to 1986 when the couple first met at a charity event in Chicago. Over the years, their love has been the topic of much speculation, both due to its longevity and their decision to maintain a private life, never officially tying the knot. However, in 1992 they did become engaged, and despite never marrying, they remain truly committed to each other, often referring to each other as life partners.

    Stedman Graham is a successful businessman, author, and motivational speaker. He is most well-known for his work in the field of education, promoting personal growth and development. With over ten books under his belt, including bestsellers like You Can Make It Happen and Identity: Your Passport to Success, he has carved a niche for himself as an expert on success and leadership.

    • Age: 72
    • Birthplace: Whitesboro, New Jersey, New Jersey
  • Randolph Cook
    Photo: flickr / CC0

    Randolph Cook

    In the early 1980s, before her rise to stardom, Oprah Winfrey had a brief relationship with Randolph Cook. The two reportedly met while working at a TV station in Nashville and dated for a short period of time. Though their relationship didn't last long, it is still remembered as one of Winfrey's earliest romantic connections.

    Randolph Cook is a former television news anchor, who was once a colleague of Oprah's during their time working together in Nashville. While not much is known about Cook's life beyond his brief relationship with Winfrey, it is clear that his connection with the media mogul was a notable chapter in both of their lives.

  • Roger Ebert
    Photo: Wikimedia Commons / CC-BY

    Oprah Winfrey and renowned film critic Roger Ebert shared a short-lived romance in the late 1970s. The pair met while working together in Chicago, and reportedly even went on a double date with Ebert's fellow film critic Gene Siskel and his wife. Although the romantic aspect of their relationship fizzled out, they remained friends and Ebert played a significant role in advising Oprah on her television career, encouraging her to pursue syndication for her talk show.

    Roger Ebert was an immensely influential film critic, and his work has shaped the way movies are reviewed and discussed in popular culture. Writing for the Chicago Sun-Times for more than four decades, he won a Pulitzer Prize for Criticism, making him the first film critic to do so. His television show, At the Movies, with fellow critic Gene Siskel brought film criticism into the mainstream, and his thoughtful, insightful reviews continue to be held in high regard.

    • Age: Dec. at 70 (1942-2013)
    • Birthplace: USA, Urbana, Illinois
  • John Tesh
    Photo: Stephen Lovekin / Getty Images

    In the late 1980s, Oprah Winfrey and musician John Tesh had a brief relationship that reportedly ended due to the strain caused by their interracial pairing. During their time together, the couple lived together in Nashville, but ultimately called it quits as they faced social pressures and comments from those around them. Though it wasn't meant to be, their relationship remains an interesting time in both of their lives.

    John Tesh is best known for his work as a musician, composer, and television personality. With a career spanning over forty years, Tesh has achieved considerable success in various facets of the entertainment industry, from hosting Entertainment Tonight to scoring music for the 1992 Barcelona Olympics. His unique blend of new age, contemporary jazz, and classical styles has garnered him legions of fans and numerous accolades, including six Emmys and four gold records.

  • Reginald Chevalier
    Photo: flickr / CC0

    Oprah Winfrey and Reginald Chevalier's brief relationship took place in 1989 after Winfrey's breakup with John Tesh. Chevalier, an aspiring actor and model at the time, met Winfrey at a charity event and they were spotted together at several events during their short-lived romance. Though the relationship was fleeting, it added to the ongoing intrigue surrounding Oprah's personal life.

    Reginald Chevalier's claim to fame largely revolves around his short-lived relationship with Oprah Winfrey. Despite aspirations to make a name for himself in the entertainment industry, Chevalier remains relatively unknown, his connection to Winfrey being his most notable foray into the public eye.