Although we’ve known Oprah Winfrey to be romantically linked to businessman and author Stedman Graham for decades, the general public hasn’t seen much of him in all this time. However, that all changed when he was spotted out with Winfrey during a recent outing in Chicago.
The rare Stedman sighting sent us on a deep dive into the couple’s longstanding relationship. From their meet-cute to their engagement to what they’ve said about supporting each other, we’re taking a look at Oprah Winfrey and Stedman Graham’s love story.
Stedman’s Recent Sighting
Let’s start with Graham’s most recent sighting. While in Chicago reuniting with her coworkers from “The Oprah Winfrey Show,” ahead of the 40th anniversary, her longtime partner popped out to take part in the festivities. He joined in for a cute photo opp with Winfrey and Chef Art Smith while holding a giant platter of fried chicken.
The picture was shared on Instagram by former show producer Jill Van Lokeren with a separate video posted on Winfrey’s own page.
Related: Oprah Says Stedman Graham Was Racially Profiled Before
Who Is Stedman Graham?
Stedman Graham is an educator, author, businessman, and motivational speaker. He’s also the founder and CEO of S. Graham & Associates and founded Athletes Against Drugs, a nonprofit that has awarded more than $1.5 million in scholarships. Graham is also an Indiana Broadcasting Hall of Fame inductee and the author of several books on identity, leadership, and personal development. His 1997 self-help book, “You Can Make It Happen: A Nine-Step Plan for Success,” made him a New York Times bestselling author.
How Did They Meet?
Graham and Winfrey met in 1986, coincidentally the same year that “The Oprah Winfrey Show” began. Winfrey revealed that she’d seen him around town with his girlfriend on numerous occasions and never paid him “much attention.” She also noted that she felt like he would’ve been a “player” because he was tall and “too handsome.” However, after meeting him alone at a mutual friend’s home and finding out that he was single, the two left at the same time, and Winfrey seized the opportunity to ask him if he wanted to go for a drink.
While he didn’t indulge (and reportedly still doesn’t drink to this day, according to O), that was the start of their romance.
Taking the Next Step…Kinda
Nearly six years later, the two announced their engagement in October 1992. In a cover story for PEOPLE at the time, Winfrey said the special moment happened when she stepped outside to greet him while he visited her at her Indiana home.
However, in news that would shock her fans, their engagement was called off—but the relationship was still on. Revealing why she didn’t go through with the engagement, Oprah later shared with Vogue in 2017 that they had called things off, as marriage “requires a different way of being in this world.”
She expounded on her rationale four years later in a 2020 letter in her O Magazine, writing: “I realized I didn’t actually want a marriage. I wanted to be asked. I wanted to know he felt I was worthy of being his missus, but I didn’t want the sacrifices, the compromises, the day-in-day-out commitment required to make a marriage work. My life with the show was my priority, and we both knew it.”
What Oprah Has Said About Stedman
Although Winfrey made a deliberate choice to stop going out in public with Stedman years ago (“every time there’s a new photograph, there’s a new story,” she said in 2018), her love for him remains strong.
In fact, since their relationship, she’s had nothing but positive things to say about the businessman. From praising him for loving and supporting her “fat and thin” to commending him on his self-confidence, she’s been overwhelmingly happy with her boo thang for a while now.
“I happen to be with a man who has always appreciated the fact that I was…considered a powerful person,” she told E! News in 2008. “[He’s] not trying to crowd in on it, not competing with it. He knows how to hold his own.”
In 2022, she described what they had as a spiritual partnership, writing in her magazine at the time that their bond was “the recognition that you’re both in the relationship to grow into who you’re meant to be as individuals as well as as a couple.”
What Stedman Has Said About Oprah
While Graham doesn’t do too many interviews about his romance with “The Color Purple” actress, during a 2019 interview on “Ellen,” he described Winfrey as a great cook, smart, and a hard worker with a photographic memory. He also addressed the narrative of being intimidated by having a partner like the famed TV host who has built up a successful life of their own.
“The thing about our relationship is that I want the best for her. I’m dedicated to her happiness. So that’s great for her, and I want her to be the best she can possibly be. And she’s done a pretty good job of doing that,” he said at the time.
He went on to say that what makes their relationship work is that he’s found his own happiness and is clear about his skills, talents, and abilities. As a result, he’s fully satisfied and able to support his partner.
“When you have a good partner that’s able to self-actualize their potential, and you’re able to self-actualize yours, then you know. One and one equals about six,” she said.
