Oprah Winfrey and Stedman Graham have been a couple for more than three decades.
They first met at a charity event back in 1986 and began dating shortly thereafter.
In the 90s, the successful couple toyed around with the idea of possibly getting married,
and Graham even proposed to Winfrey. Ultimately, the idea of walking down the aisle together never
actually led anywhere. Despite setting a tentative wedding date, the pair decided to call off the big
event. They felt it was best for both of them if they kept their relationship exactly as it was.
In a 2017 interview with Vogue, Winfrey revealed that staying unmarried all of these years
has taught her to live life on her own terms. She also told the outlet that she
and Graham wouldn't have lasted so long as a couple had they decided to tie the knot.
She went on to say,
"We would not have stayed together, because marriage requires a different way of being in
this world. His interpretation of what it means to be a husband and what it would mean for me
to be a wife would have been pretty traditional, and I would not have been able to fit into that."
And so, Winfrey and Graham have been together through thick and thin, but they've managed to
do so while never becoming husband and wife. They've traveled the world together, too, but,
believe it or not, they've rarely taken a vacation when it's just the two of them.
As one of the wealthiest women in the country, it's no surprise that Winfrey is well-traveled.
However, the television legend has always shared her vacations with a
very special person in her life — her best friend,
Gayle King. In fact, the two of them have been vacationing together since 1993.
In a show called "The OG Chronicles: Joy Ride,"
Winfrey and King discussed the fact that King has been included in every single
vacation that Winfrey has taken — with or without Graham — for almost 30 years.
During the episode, King told Winfrey that when they're on vacation with Graham, she feels like
the three of them have a wonderful time. She also mentioned that if she was the third wheel,
she didn't know it and if Graham didn't like her, it would have been tough.
Winfrey had a quick answer to that, however,
letting King know that if Graham didn't like her, he would have been out the door.
Winfrey and King both said...
"Husbands come and go.
Boyfriends come and go. But best friends, best friends last forever." "Forever."
Proving that point, Winfrey and King have been friends for more than 40 years.
In July of 2021, the two women filmed a video in which they addressed their long-lasting friendship
and shared it on Oprah Daily's Instagram account.
Winfrey said…
"Surround yourself with someone who is as happy for your happiness as you are for your happiness."
She also shared this bit of wisdom:
"You need friends that are happy in their own
lives so that they can actually be authentically happy for you."
In an interview for Oprah Magazine in 2006,
the ladies revealed that they talk on the phone with each other about four times
every day. It's no secret that Winfrey and King have been in each other's lives for so long
because they love and support each other through all the various ups and downs that come their way;
and we're sure that the adventures they've shared are ones that they'll both cherish forever.
However, there are certainly some trips that have been more memorable than others.
For instance, the two took an epic 11-day cross-country road
trip from Santa Barbara to New York City back in 2006. In 2014,
the ladies traveled to Italy where they picked truffles to their hearts' content.
A year later, Winfrey and King jetted to Ibiza for a gorgeous and upbeat party trip.
Perhaps one of their favorite excursions was the one they took to Fiji in 2015.
Winfrey and King headed to the South Pacific to celebrate King's 61st birthday.
This trip was extra special because Stedman Graham was along for the festivities,
which included nature walks, swimming — and, of course, a birthday cake.
With or without Graham, there's no doubt that Winfrey and King are
B.F.F.s who know how to make vacation memories that will last a lifetime.
Check out one of our newest videos right here! Plus,
even more Nicki Swift videos about your favorite celebrities are coming soon.
Subscribe to our YouTube channel and hit the bell so you don't miss a single one.