Oprah and Gayle Go on a Road Trip 15 Years After Their Famous Cross-Country Trek

Oprah and Gayle Go on a Road Trip 15 Years After Their Famous Cross-Country Trek

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In 2006, Oprah and Gayle drove from Santa Barbara, California to New York City. Their cross-country road trip was captured for The Oprah Winfrey Show and was filled with moments viewers would never forget, including a notorious Celine Dion singalong and the crashing of two weddings. Paying homage to the original road trip, this summer the O and G of The OG Chronicles reunited for another adventure on the road, albeit a shorter one.

15 years later, the vaccinated—and Covid cautious—best friends have come together for a multi-stop adventure through Santa Barbara that they dubbed “The OG Chronicles: Joy Ride.” Since Oprah freely admits she doesn’t love driving, Gayle stayed in the driver’s seat this time around. “Tell the people: You don’t like to merge! You don’t like to pass cars! You don’t like to be on the highway!” Gayle tells her best friend at the beginning of the video, part one of a three-episode OG Chronicles extravaganza that we’ll be dropping right here on OprahDaily.com each Thursday for the rest of September. “That’s why I’m not driving,” Oprah responds. Simple as that.

Sitting side-by-side in a Lexus ES 350 F Sport, Oprah and Gayle’s first stop was to visit Arlene Ramirez, a charter member of our Oprah Daily Insiders community who lives nearby in Santa Barbara. “I think it’s great these Oprah Insiders signed up for all things that help you move toward a better life,” Oprah says. To pass the time during their drive, Oprah and Gayle answer questions from other friend duos, starting with longtime friends Andy Cohen and Anderson Cooper.

For context, Oprah shares a fun fact: CNN’s Cooper and Bravo’s Cohen first met after they were set up on a date 20 years ago. A romance didn’t develop, but a friendship did. “I can’t imagine dating you either,” Gayle quips to Oprah after hearing Cooper and Cohen’s friendship meet-cute.

Since Cohen and Cooper often travel together for their tour “An Intimate Evening With Anderson Cooper and Andy Cohen,” they admit they experience the occasional bouts of tension. So in their question for Oprah and Gayle, they want to know how to deal with similar stresses during friend trips. “There were always moments where Oprah seemed done with Gayle,” the friends commented. “What is the moment that sticks in Oprah’s mind where she was the most annoyed with Gayle?”

Oprah’s response? Back in 2006, as they were finally nearing New York, Gayle’s singing became so irritating to Oprah that she requested a football helmet to block the noise. “I’m not kidding. I would like a football helmet. I’ve got earplugs. I’ve got earphones. I’m going to put on plugs and a helmet. That’s the only thing that can help me,” Oprah said while on the phone with security.

After reminiscing about that memory, Oprah and Gayle address a question from an Oprah Daily Instagram follower @legacycompressions who says she’s hurt that her best friend of 27 years will take trips with her boyfriend…but not with her. “Whenever I suggest we take a girls’ trip, she says she doesn’t have the money. I’m a little bothered by this. Should I be?” she asks.

Gayle admits that were she in the letter-writer’s situation, she’d be bothered by not feeling as if she were a priority in her best friend’s life. But as Oprah points out, Gayle has never experienced taking a backseat to her best friend’s romantic partner. Gayle has always been included.

In fact, since her divorce in 1993, Gayle has been on every vacation that Oprah has taken with her partner, Stedman. “The three of us have had a wonderful time. If I was the third wheel, I didn’t know it!” Gayle says. “If Stedman didn’t like me, that would’ve been tough.”

For Oprah, Stedman liking Gayle was a non-negotiable. “If Stedman didn’t like you, Stedman wouldn’t have lasted. Husbands and boyfriends come and go. Best friends last forever,” she says.

After all the advice-giving on California’s 101 highway, Oprah and Gayle arrive at their first destination. They pull into the driveway of Oprah Insider Arlene Ramirez, who thinks she’s on a Zoom call with Oprah Daily’s Shelby Copeland for an Oprah Insider event. Little does she know the Zoom is just a distraction—and then, the doorbell rings.

“Sorry, someone’s at the door,” Ramirez says. And then she opens her front door to see…Oprah and Gayle. “What is happening?!” Ramirez exclaims. “Did I win the lottery?!”

Oprah hands Ramirez a basket of produce—including avocados, apples, heirloom tomatoes, lemons, and roses—hand-picked from her garden, plus jars of honey from her home in Maui. A stunned Ramirez tells Oprah she played a major role in her personal evolution. Oprah, she says, helped her learn to love herself.

“You have to love yourself first before you can start giving it to others,” she says, echoing Oprah’s words. “I didn’t know before. I didn’t want people to not like me.” Ramirez says this change of perspective has impacted her relationship with her daughters, Marynicole and Jacqueline. “I can share [the love] with my girls and their friends.”

After taking a selfie with Ramirez and her daughters, Oprah and Gayle hit the road again. Up next? Oprah and Gayle have one more Oprah Insider to visit—but first, they have an errand to run: Shopping for Gayle’s soon-to-be grandson…with a little help from a certain Santa Barbara celebrity. Stay tuned!

Originally posted on OprahDaily.com: Oprah and Gayle Go on a Joy Ride 15 Years After Iconic Road Trip

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