The two buds have been together since Day 1, before the fame and when they were both struggling journalists. Since skyrocketing to professional nirvana, the two have leaned on each other for various business ventures. Gayle works as editor-at-large at O, The Oprah Magazine, and she was a guiding force on The Oprah Winfrey Show (she appeared on the talk show a staggering 139 times!).
Who could forget Oprah and Gayle’s memorable 2006 road trip? The two loaded up their red Chevy Impala and embarked on a 3,000-mile roadtrip (yikes!). Their journey was hefty, but these two besties had the time of their lives, stopping in small towns, playing bingo with locals, channeling their inner cowgirls and crashing a wedding. We’re using their adventures as a roadmap—literally—for our next road trip.
The only thing stronger than Oprah’s unshakeable relationship with longtime beau Stedman Graham is her friendship with Gayle. Oprah has never let her relationship take precedence over her friendship, which is perhaps the number one rule of bestiehood.
You can take the girl out of the party, but you can’t take the party out of the girl! Last night, Oprah and Gayle were spotted living it up in Ibiza, Spain, taking shots and dancing the night away. There’s nothing like a good girlfriend to remind you that no matter what, you’re still young at heart.
Camping in Yosemite may sound nightmarish to some, but factor in a girlfriend and loads of laughter, and it automatically becomes paradise. Whether they’re pitching a tent in a national park, truffle hunting in Italy, getting cozy with koalas in Australia or living a colonial lifestyle in Maine, Oprah and Gayle know how to embrace their circumstances and turn it into an experience to remember.
It wasn’t always glitz and glamour for these two. Oprah and Gayle have worked hard to achieve their successes, and they have always been able to use each other as stepping stones. Gayle has helped take Oprah’s magazine to new heights, and Oprah has done wonders for Gayle’s own career. There’s no room for selfishness in this friendship.
It was no shock that Oprah had a few surprises up her sleeve for Gayle’s 60th birthday in December. She threw her girlfriend the ultimate soiree in New York City… but the celebration didn’t stop there! When the two took a trip to Hawaii later that month, Miss Winfrey surprised Gayle by flying her sisters, nieces and nephews to the island paradise. A Hawaiian excursion might be a little extreme, but a little girlfriend gift never hurt anyone!
In 2007, Oprah invited 60 women who have experience hardships to Miraval Spa, a luxe Arizona resort to give the women an opportunity to relax, rejuvenate and get out of their comfort zones (Swing and Prayer, anyone?). And, of course, she brought Gayle with her, reminding us that it’s okay to indulge in a girls day every once and a while. You ladies have earned it!
The besties had the ultimate New Years Eve plans last year: They had flown to Hawaii to ring in 2015 the island way. However, their plans were diverted after Gayle sprained her ankle just hours before midnight. Oprah accompanied her pal to the emergency room, and stuck around to make sure she was taken care of (and judging by Gayle’s Instagram pic, it looks like somehow, they still managed to have a good time).
Biologically, Oprah and Gayle aren’t sisters, but they might as well be. At some point throughout the years, the two families blended into one—it’s not uncommon for Oprah and Stedman to spend major holidays with Gayle and her children. If we didn’t know any better, we would think that they were simply one, big family. If that’s not #SquadGoals, we don’t know what is!
