Oprah Winfrey and her best friend Gayle King have spilled the beans about having one-night stands in the early 1980s while playing a game of ‘Never Have I Ever’ with Ashley Graham.
On the latest episode of OprahMag.com’s ongoing video series, The OG Chronicles, the 32-year-old model moderated the game and asked them juicy questions about sexting, playing hooking from work, and lying to each other.
The best friends proved that they aren’t exactly wild at heart, with Oprah, 66, insisting she has never once played hooky from work. However, they both fessed up to having one-night stands, and Gayle admitted she once lied to Oprah about where she was — though she wouldn’t’ admit why.
Fun times: Oprah Winfrey (left) and Gayle King (right) played ‘Never Have I Ever’ with Ashley Graham (center) on the latest episode of The OG chronicles
Rules: As part of the game, they had to hold up one hand. If they had done the ‘Never Have I Ever’ question, they had to put a finger down. The first one to put all five fingers down lost
At the start of the video, Ashley walked them through the rules of the game, explaining that they have to hold up one hand. If they have done the ‘Never Have I Ever’ question, they have to put a finger down. The first one to put all five fingers down loses.
The Pretty Big Deal podcast host pointed out that it’s supposed to be a drinking game, but since Gayle doesn’t drink alcohol, they decided the loser has to take a shot of either apple cider vinegar or Oprah’s favorite Truff Hot Sauce.
For her first question, Ashley asked if they have ever stalked someone on Instagram — something nearly everyone has done at least once — but the friends insisted that they never have.
‘What? I feel like you guys are lying,’ Ashley said before explaining what Instagram stalking is to Oprah, who couldn’t figure out why anyone would want to do that.
The author went on to ask the on-air personalities about playing hooky from work. While Oprah said she ‘never’ has, Gayle admitted to doing it — just once.
‘It was a long time ago. It was a mental health day,’ she said.
‘Just put the finger down,’ Oprah told her.
Gayle couldn’t believe that Oprah had never once skipped out on work, but she insisted she hadn’t.
‘I have never not gone to work. Listen, for 25 years, I did not miss a fricken day,’ she said of the time she spent hosting The Oprah Winfrey Show. She also noted she never called in sick when she wasn’t sick before or after her talk show.
Surprise: They both confessed to having one-night stands in the ’80s. They are pictured with Oprah’s longtime partner, Stedman Graham, in 1994
‘I believer her,’ Ashley said.
Oprah and Gayle, the host of CBS This Morning, have both interviewed their fair share of people over the years, so it made sense that they were both asked if they had ever interviewed someone they dislike.
‘Oprah, you have interviewed people you dislike. You better put that finger down,’ Gayle told her, though she kept her remaining fingers up.
Their next juicy question was about ‘sexting with someone,’ and they both said ‘definitely not.’
‘You haven’t sexted with Stedman [Graham]?’ Ashley asked in shock.
‘Hell no! Are you kidding me? I’d be a fool,’ Oprah said.
‘If she put her finger down on that, I’d pass out on the floor right now,’ Gayle added before asking Ashley: ‘Have you?’
‘Of course I have! Justin and I get into it,’ she said of her saucy relationship with her husband, Justin Ervin.
‘But you never know where that picture is going to end up,’ Gayle stressed, and Oprah agreed.
Dedicated: Oprah, 66, insisted she never called off work once in her career. She is pictured on The Oprah Winfrey Show in 1993
TV starsL Oprah revealed she had interviewed someone she disliked, but Gayle, the host of CBS This Morning, claimed she hadn’t
Ashley briefly tried to argue her point but thought better of it and moved on, asking them: ‘Never have I ever pretended to know a celebrity I really didn’t know.’
While Gayle hadn’t, Oprah admitted it’s a regular occurrence for her.
‘I do it all the time. I don’t know anybody, so I’m like walking through the crowds going, “Hey! How you doing?”‘ she said.
‘And we’ll say, “She’s been on your show before. He’s been on your show before,”‘ Gayle added.
Considering Oprah is one of the most famous people in the world, this seems like a move that only she could pull off time and time again.
Ashley went on to ask the TV stars if they’ve ever thought about having plastic surgery, and Oprah said she has ‘definitely thought about it.’
Gayle put her finger down too, but then she changed her mind and put it back up, saying: ‘I don’t think I’ve thought about it.’
Things got really interesting when Ashley asked if they had ever had a one-night stand.
‘We both better put our fingers down on that one,’ Gayle said with a laugh.
Not having it: Oprah insisted she had never ‘sexted’ Stedman, saying she would be a ‘fool’ to do so because you never know ‘where that pictures is going to end up’
Keeping it real: Ashley, 32, said she and her husband, Justin Ervin, sext and ‘get into it’
‘Mine would have been ’82, something like that,’ said Oprah, who met her longtime partner Stedman in 1986.
Gayle calculated that hers was around the same time, saying: ‘Let’s see. It was Kansas City. It would be ’82 or ’81.’
After the first round, Oprah was the clear loser, and she opted to take a shot of apple cider vinegar, cringing the entire time.
‘It makes my nipples hard when I drink that stuff,’ Ashley admitted.
‘What happened to the fun part? The tequila part,’ Oprah wanted to know.
Ashely kicked off the second round by asking Oprah and Gayle if they had ever lied to their best friend about where they were — a loaded question considering they have been best friends for over 40 years.
‘Never! why would I do that?’ Oprah asked, but Gayle looked very guilty when she put her finger down.
Oprah noted that she knew what had happened, saying, ‘That story is so good,’ but Gayle wasn’t up for telling it.
‘I’m just gonna put my finger down,’ Gayle said.
Yuck! After losing the first round, Oprah had to take a shot of apple cider vinegar
Cringing: ‘What happened to the fun part? The tequila part,’ Oprah wanted to know
‘I have not, but you definitely have,’ Oprah added. ‘You know what? You should put two fingers down for that.’
Ashley went on to ask them if they have ever returned an item of clothing after wearing it. Oprah once again said no, but Gayle had.
‘When I was younger…I might have just worn it one time. I was younger,’ she explained. ‘I am ashamed. It was in my 20s.’
They both fessed up to regifting gifts: Oprah said she regifted a vase while Gayle got rid of a curling wand.
When asked if they had ever skinny-dipped, Oprah said she had not, which her companions found a bit hard to believe considering how many private homes she owns.
‘Not at your own pool at home?’ Ashley asked.
‘No, and I got three,’ Oprah noted.
‘Does a hot tub count as skinny-dipping?’ Gayle asked before putting a finger down.
The game also revealed that neither of them had ever been to a strip club or pole-danced before. Oprah wasn’t even confident she knew what a strip club was.
‘A strip club is when people take their clothes off, right?’ she confirmed. ‘I definitely have not done that.’
Oprah couldn’t resist joking that she was going to get Gayle a pole for her next birthday, a perfect gift for ‘the woman who has everything.’
‘If it comes with a man, do that,’ Gayle said.
For their last question, they were asked if they had ever lied during ‘Never Have I Ever.’ Since neither of them had ever played before, Ashley basically wanted to know if they had lied to her.
‘It’s a game. We didn’t lie in this game,’ Oprah assured her.