Red Flags In Oprah & Stedman's Relationship We Can't Ignore

Oprah Winfrey and Stedman Graham have been together for what feels like forever. But they're proof that a long-lasting relationship isn't always devoid of red flags, because theirs is full of oddities. One of the most notable is that Winfrey and Graham never married, despite meeting in 1986 and getting engaged in 1992. "Stedman just proposed!" Winfrey gushed to her best friend Gayle King, according to People, before the star confirmed Graham told her, "I want you to marry me. I think it's time." However, the two eventually called off their engagement but stayed together, with Winfrey telling Oprah Daily, "The moment after I said yes to his proposal, I had doubts. I realized I didn't actually want a marriage. 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."

Though never marrying isn't necessarily a red flag (it's not for everyone, and that's okay), Graham made it clear he wanted to take things to the next level, and Winfrey going back on her word suggests he compromised for her. Something as important as marriage isn't something to compromise on, though, especially if it's because the other person isn't willing to put in the effort. Certified relationship expert Anna Williamson told Hitched, "There really is no right or wrong way to commit to someone, but what is important is that both people are on the same page and have the same ideas and goals about what their future looks like." Winfrey and Graham? They clearly weren't on the same page. But their red flags go way deeper than just never making it down the aisle.

25 years after Stedman Graham proposed, Oprah Winfrey told Vogue that she didn't think they'd still be together if they'd walked down the aisle. And that's a red flag. The former talk show host suggested they hadn't spoken about marriage again since they called off their nuptials, sharing, "Nobody believes it, but it's true. The only time I brought it up was when I said to Stedman, 'What would have happened if we had actually gotten married?' And the answer is: 'We wouldn't be together.'" Winfrey underscored that to Oprah Daily in 2020, explaining, "Marriage requires a different way of being in this world. His interpretation of what it means to be a husband and what it would mean for me to be a wife would have been pretty traditional, and I would not have been able to fit into that."

Winfrey admitting their relationship wouldn't have survived marriage is certainly eyebrow-raising. Though marriage is a big commitment and shouldn't ever be entered into lightly, if Winfrey and Graham are truly committed to one another and plan to spend the rest of their lives together, a walk down the aisle shouldn't have changed how they felt about each other. It also shouldn't have altered their dynamics drastically enough to cause a breakup.

Oprah Winfrey has made no secret of putting her career above her relationship with Stedman Graham. In a piece for Oprah Daily, she explained another reason they never married was that work was more important to her. "My life with the ['The Oprah Winfrey Show'] was my priority, and we both knew it," she said. Graham has publicly supported her career and even said on "The Ellen DeGeneres Show" in 2019, "I'm dedicated to her happiness, so that's great for her, and I want her to be the best she can possibly be."

But a consistently busy work life can have a serious effect on personal relationships. We can't fault Winfrey for chasing her dreams, but sometimes, it's okay to say no at work to ensure your relationship is thriving, too. It's imperative that the TV producer maintain a healthy work/life balance and regularly show Graham he's a priority as well. Otherwise, as the years roll on, he could feel increasingly resentful and undervalued if he's constantly taking a backseat to her work projects.

Though it's not unusual for PDA to slow down over the years, Oprah Winfrey's stepmom, Barbara Winfrey, dropped some major bombshells about how her stepdaughter and longtime love behave behind the scenes. Winfrey's stepmom told Daily Mail she'd never seen the couple be affectionate toward one another, including no handholding or kissing. "He was comfortable like an old shoe, to her. They stayed in the same room when they were here, but he didn't live with her exactly," she claimed.

Not everyone enjoys taking part in PDA (honestly, we don't enjoy seeing it with every celeb either), and that's fine, but it's a red flag if someone who's known Winfrey and Stedman for decades has never seen something as simple as a comforting handhold. Though everyone has different preferences regarding the five love languages, physical touch can be key in keeping the passion alive and romantic relationships strong. "Many studies in neuroscience show that touch produces oxytocin, a feel-good chemical that is very good for your mental and physical health," Silva Neves, a COSRT-accredited psychosexual and relationship psychotherapist, told Cosmopolitan U.K. If Winfrey and Graham never show affection, they could risk their romantic relationship plateauing and turning into a friendship.

Couples' vacations should be sacred times to spend quality time alone together. But that's not a luxury Oprah Winfrey and Stedman Graham enjoy. On "The OG Chronicles: Joy Ride," Winfrey confirmed she'd never vacationed just her and Graham since King split with her former husband, William Bumpus, in 1993. "Since after your divorce, you were on every vacation with me and Stedman," Winfrey said (via Daily Mail). King responded, "The three of us have had a wonderful time. If I was the third wheel, I didn't know it! If Stedman didn't like me, that would've been tough." Winfrey then retorted, "If Stedman didn't like you, Stedman wouldn't have lasted. Husbands and boyfriends come and go. Best friends last forever."

King has also made it clear she has no plans to let the couple enjoy their alone time. "I'm a proud third wheeler. I make no apologies for that ... throughout the years, we've gone on some great trips together. And that's not gonna change," she told Entertainment Tonight.

Though we can't fault the importance Winfrey and King put on friendship, King's omnipresence could cause problems. By making every trip friend-friendly, Winfrey risks changing the dynamic of her romantic relationship. "Connection thrives on exclusivity. When your partner blurs the lines between being your lover and being one of the group, you risk losing the dynamic that makes your bond unique," relationship expert Dr. Channa Bromley told Daily Mail. Always having the "CBS Mornings" host around (as much as we love her) could also quell the quality time Winfrey and her partner can spend just the two of them — and that could be detrimental to their romance.

Money issues can often cause problems between couples, and while we doubt Oprah Winfrey and Stedman Graham are falling out about not having enough of it, the vast gap between their net worths could be problematic. According to Celebrity Net Worth, Winfrey has amassed an eye-watering $4 billion, while Graham has a more modest $10 million. It's surprising, then, that Barbara Winfrey claimed Graham relied a lot financially on her stepdaughter. "Stedman isn't a good steward of money, and that suits Oprah fine. He is financially dependent on her," she told Daily Mail.

Graham supposedly being financially dependent on Winfrey could be a red flag. It may mean Graham doesn't feel he could end their relationship if he wanted to, and could also create a power imbalance between them. "Both partners, regardless of the difference in income or financial know-how, should probably at least have some involvement in managing the household's finances," LendingTree chief consumer finance analyst Matt Schulz said.

Spending could also cause problems. Architectural Digest reported Winfrey's real estate portfolio alone is worth 10 times Graham's net worth. If she feels she's consistently bankrolling their lifestyle with little or no financial input from her partner, she could become resentful. Equally, if Graham can't keep up with Winfrey's lavish lifestyle, that could be an issue too. "Money is not only a common cause of conflict, but money fights are qualitatively different from other types of arguments. They tend to last longer and are less likely to get resolved, so they create tension leading to other arguments and spending less time together," Megan McCoy, certified financial, marriage, and family therapist, and Kansas State University assistant professor of personal financial planning, told Fortune.