The 66-year-old broadcaster - who has adult children Kirby and William with ex-husband Bill Bumpus - admitted it wouldn't "occur" to her that she wouldn't be invited on vacations with her best friend Oprah and her long-term partner Stedman because they have always been so "welcoming" towards her.
She admitted, "I'm a proud third wheeler. I make no apologies for that. I got divorced back in 1994 and I've been their third wheel ever since."
"The good news is that Stedman is always very welcoming, so it never occurs to me when she says, 'We're going to so and so,' I'm like, 'When?' It doesn't occur to me that I'm not invited."
"But throughout the years, we've gone on some great trips together. And that's not gonna change."
The two friends always put their bond ahead of any relationship.
Gayle told Entertainment Tonight, "Oprah came to my house after my favourite daughter, Kirby, was born and she was wearing a T-shirt that said, 'Husbands come and go, best friends last forever,' and I went, 'Whoa, why are you wearing that T-shirt?' She didn't even realise, she said she didn't even realise she had it on, but there is some truth to that."
"When you have a best friend, you really are there through thick and thin, and that's not always true with husbands and spouses or you know, co-workers, anybody in your life, but when you have a true best friend, it really does. It is something that really is a lifelong thing."
After embarking on a cross-country trek 15 years ago, the two women have embarked on another road trip for new series "OG Chronicles: Joy Ride" and Gayle knew all along she'd be the one taking the wheel.
She said, "She ain't changed. She doesn't like to merge, she doesn't like to get on the highway, she doesn't like to parallel park, man, she doesn't like to change lanes, all the things that come with...driving!"
"I really enjoy driving. I actually do, but what I really like is the rule that if you're behind the wheel, you get to control the radio!"