Strange Things About Oprah And Gayle's Friendship

Being one of Oprah Winfrey's BFFs sounds like a dream come true for most, but there's only one person who gets to hold this honor. Her name is Gayle King, and she's the jelly to Winfrey's peanut butter, her ride or die, and a permanent fixture in the media mogul's life.

Oprah and Gayle's relationship started off like most friendships. They were complete strangers up until they became coworkers at a Baltimore television station in the 1980s. Since then, they've proven their loyalty to one another and have gone on to intertwine their personal and professional lives, with King acting as the editor-at-large for Winfrey's O, the Oprah Magazine, and Winfrey snagging the title of godmother to both of King's children, William and Kirby.

With a bond that runs deeper than a regular friendship, they've managed to raise a few eyebrows from their critics, as well. Some naysayers are convinced there must be a hidden, more salacious reason they're joined at the hip.

Their closeness, as well as these strange things about Oprah and Gayle's friendship, definitely pings our creep-o-meter from time to time.

It started with a snowstorm and shared underwear

Their friendship began when they were in their early 20s and both employed at a television station in Baltimore — with Winfrey working as a news anchor and King as a production assistant. 

A huge snowstorm hit their area, and out of the kindness of her heart, Winfrey offered to allow King to stay at her home instead of having her making the 45-minute drive back to her house. "We didn't really know each other," King told the Huffington Post, "but she was just that kind of girl even then."

They wound up talking all night long, discovering so much about one another in the process. "We found we have very similar philosophies about life and people. And we realized we liked and disliked the same people in the newsroom, which was interesting," King told the Seattle Times.

Not only did Winfrey allow King to stay with her, but the future daytime talk show host made sure all of her new BFF's needs were met. "When I said didn't have any clothes with me, she said, 'You can wear mine,' and when I said I didn't have any underwear she said, 'You can borrow mine, it's clean!" King told the Huffington Post.

Okay, sharing clothes is perfectly fine, but the thought of sharing underwear with anyone, let alone a stranger, makes us itch in places we'd rather not mention.

Constant contact and an auntie suite

Winfrey and King are quick to dish out all the details about their long-lasting, storied friendship. However, some of the juicer rumors about their relationship came courtesy of a woman named Barbara — who just so happened to be Winfrey's ex-stepmother.

After Barbara and Winfrey's father, Vernon, were married in 2001, the talk show host bought the former couple a sprawling $1.4 million home, according to USA Today. When their marriage hit the skids 14 years later, Winfrey attempted to evict Barbara from the house but eventually gave the woman 60 days to vacate following a judge's recommendation. 

In what could be seen as retaliation on Barbara's behalf, she opened up to the Daily Mail for an exclusive, no-holds-barred interview to spill the tea. Barbara reportedly called Winfrey and King's friendship unhealthy and revealed the duo would speak on the phone up to three or four times a day. Let's just hope they have unlimited talk times with their cell phone plans!

We're not sure how either of them are able to squeeze so many calls in with their packed schedules. To make things even more strange, they reportedly chat all day long despite co-habitating in one other's homes. The Hartford Courant reported in February 2001 that Winfrey had her own "Auntie O's" suite inside of King's South Glastonbury, Conn. home. 

Creepy much?

Three's company

Back to that aforementioned interview Winfrey's ex-stepmother gave to the Daily Mail. Barbara also dropped some gems about the dynamics that exist between Winfrey, King, and Winfrey's long-term partner, Stedman Graham, whom she's been dating since 1986 after meeting at a charity event.

Even while King was married to her ex-husband, William Bumpus Sr. — who she famously caught in bed with another woman on "June 24, 1990, at 9:16 p.m." (but really, who's keeping track?) — King has spent a lot of time tagging along as the third wheel in Winfrey's relationship. 

Barbara described an 11-day Mediterranean cruise the entire family took, and told the publication, "[Winfrey] didn't spend any time with us. It was always her, Stedman and Gayle. The three of them. Anytime you looked up they were together. To me it was just bizarre." Bizarre indeed.

While most people would be a bit peeved if their partner's BFF was a constant shadow in their relationship, Stedman doesn't seem to mind. "Gayle is very, very present. I don't know any man I've ever dated who could tolerate that, but Stedman knows Gayle's going nowhere," Barbara said.

What not to wear

When it comes to their bond, Winfrey seems to dish out unsolicited advice on the regular because a good friend should always tell their bestie when they're looking like a hot mess, right? 

Being brutally honest is Winfrey's forte, as we all know. She makes a living saying the right things at the right time, and her caring and loving approach has solidified her role as the best friend we all wish we could have. But when it comes to King, Winfrey doesn't mince her words. At. All.

In one incident, King decided to wear an emerald green top and an oversized necklace while filming CBS This Morning. When Winfrey tuned in and spotted her best friend's accessory choice, she wasted no time giving her feedback.

In an Instagram post, King reposted a screenshot of her outfit, along with a caption that read, "Note @oprah sent to my [assistant] this am "plz tell Gayle I'm on treadmill & it's hard to focus w/the circus around your neck" I think she's WRONG thoughts?"

We know Winfrey has King's best interests at heart, but that note was a bit too harsh and, dare we say, flat-out rude.

Shady makeup tips

It's not just jewelry advice that King receives on the regular, Winfrey also tells it like it is when it comes to King's makeup, as well. During a November 2015 taping of CBS This Morning, King decided to shake things up in the beauty department by wearing a bright-colored lipstick on set. And once again, Winfrey wasn't pleased.

King posted another screenshot from the taping to her Instagram page, along with the caption: "@Oprah just called & said tell your makeup artist waaaay too red on the lips today and I said proudly 'I did that MYSELF' Dead silence on the line ... Hello ??hello?..." Ouch.

We're sure Winfrey is only looking out for her bestie because she wants her to look her best at all times. However, maybe she's a bit too critical when it comes to King. There's nothing wrong with having an opinion, but isn't she crossing the fine line from constructive criticism to Shady McGrady?  

Birthdays bring out the worst in them

Surely friends who spend the majority of their time together are bound to have petty tiffs from time to time, and Oprah and Gayle are no different. During an episode of The Oprah Winfrey Show, the talk show maven invited King for a sit-down interview to discuss all the ins and outs of their friendship.

Winfrey admitted, "I'm not big on birthdays, [King] is," before admitting, "Some of our biggest fights have been about birthdays."

So what is it about birthdays that causes tempers to flare? Well, after Winfrey revealed their most heated topic of discussion, King replied underneath her breath, "Birthdays should be acknowledged ... I'm just saying," and Winfrey responded with, "I now know that."

Let's dissect: It sounds like on one of King's birthdays, none of Winfrey's three or four phone calls of the day included a birthday salutation. And honestly, that would make us a bit peeved, too.

Gayle is the mother she never had

Winfrey has been very open about her childhood over the years, including the fact that she was raised by her grandmother in Mississippi for the first years of her life. She was sent to live with her mother, Vernita Lee, in Wisconsin when she was 6 years old. And later, she was sent to live with her dad, Vernon, in Tennessee at the age of 9, before returning to live with her mother once again. As you can imagine, things at her various places of resident were far from idyllic.

"I ran away from home. I started acting out my need for attention, my need to be loved. My mother didn't have the time. She worked every day as a maid," Winfrey told the Washington Post.

Years later, with King by her side, Winfrey finally felt the love and sense of protection and stability she always craved. She told ABC's A Barbara Walters Special: Oprah, The Next Chapter about her friendship with King: "She is ... the mother I never had. She is ... the sister everybody would want. She is the friend that everybody deserves. I don't know a better person."

We're glad Winfrey was able to find everything she needed in her friendship with King. But wearing so many hats has to come with a lot of stress. We just hope King doesn't crack from the pressure.

Move over, Dr. Phil — there's a new therapist in town

With Winfrey living through the type of childhood that you wouldn't wish on your worst enemy, which comprised of the star getting pregnant at the age of 14 and intending to commit suicide, it's not surprising that she may need a shoulder to lean on from time to time. Fortunately, King gladly steps in to comfort her friend.

During a 2010 interview with Barbara Walters (via E! News), Winfrey admitted she never sought out a professional to help her work through the inner turmoil she struggled with. "The therapy that I didn't have, and the therapy that I don't need, is because of my thousands and thousands of hours on the phone with Gayle," she said. Well, that explains the incessant phone calls.

Nothing can replace a professional's help, and we can't imagine how much weight is on King's shoulders as Winfrey's personal sounding board. However, being Winfrey's trusted confidante also comes with its own set of perks ... strange perks, might we add.

The truth about Winfrey's $1 million gift

During the height of her daytime talk show, Winfrey showered her audience members with lavish gifts, such as houses, cars, and college scholarships. Her generosity towards strangers is unmatched, and she's displayed this same altruism when it comes to her bestie.

King appeared on an episode of Bravo TV's Watch What Happens Live, and she was asked by a caller to describe her all-time favorite "thing" from Winfrey. "After I had my second baby — and [my kids are] 11 months apart, where you say to the doctor, 'I thought this diaphragm was supposed to work — [Winfrey] gifted a live-in nanny," King told the show's host.

King admitted she would've never been able to afford the nanny if it weren't for Winfrey's generosity, which King called "a good gift."

However, despite Winfrey being the godmother of King's kids and a fairy godmother of sorts to the CBS This Morning host, she apparently isn't making it rain on King like many of us assume.

Rumors began circulating that Winfrey once gifted her best friend with $1 million so she could become a millionaire, too. "I just think that's funny," King told the Seattle Times in an attempt to dismiss the rumor. "One million dollars ... She's been very generous. You see how generous she's been with strangers, so you know how she must be with me. Let's just say I live a very, very nice life. A very nice life."

Dodging lesbian rumors

Because they rarely leave each other's side, Oprah and Gayle have had to dispel rumors that they're in a romantic relationship. "I'm not a lesbian ... I'm not even kind of a lesbian," Winfrey told Barbara Walters. "And the reason why it irritates me is because it means that somebody must think I'm lying. That's number one. Number two ... why would you want to hide it? That is not the way I run my life."

It wasn't the first time she had to address the speculation. In an issue of O, The Oprah Magazine, Winfrey continued, "I understand why people think we're gay. There isn't a definition in our culture for this kind of bond between women. So I get why people have to label it — how can you be this close without it being sexual? How else can you explain a level of intimacy where someone always loves you, always respects you, admires you?"

Even King addressed the rumors after Rosie O'Donnell alluded to the duo being the "emotional equivalent" of a gay couple during an interview with Howard Stern's Sirius XM show. King told Access Hollywood in November 2009, "The thing [is], if we were gay, we would tell you ... The truth of the matter is we're not. It's hard enough for me to get a date on a Saturday night as it is. This isn't a rumor I'm trying to continue to explore, but no there's nothing, there's nothing wrong with it."