While her life has not always been easy, she has ensured that she has a giving spirit and tries to do as much as she can for those less fortunate than she.

WINFREY’S PREGNANCY AND HER MOTHER’S DECISION

Winfrey fell pregnant at age fourteen and hid the pregnancy for seven months until the child was born. She shared in her “Life Class” program for OWN that she saved the unborn baby because she felt detached:

“I saved that baby because I was so disassociated and still do feel such a disassociation. I never felt like it was my baby.”

Oprah Winfrey at the “Greenleaf” Press Conference held at the Four Seasons Hotel on September 26, 2016 in Beverly Hills, California. | Source: Getty Images

Winfrey admitted hiding the pregnancy brought her nothing but shame and that having swollen ankles and a big belly made it evident that she was expecting:

“I was so ashamed. I hid the pregnancy until my swollen ankles and belly gave me away.”

“Hiding that secret and carrying that shame blocked me in so many ways that I remember being taken to the detention home when my mother was going to put me out of the house at the age of 14,” Winfrey continued.

She talked about the overall ordeal and how it made her feel at the time and said: “The experience was the most emotional, confusing, traumatic of my young life.”

Winfrey further explained that being taken to the detention home and waiting to be processed while there, she remembered how relatives abused her from age nine.

The media mogul disclosed that she had been sexually abused at nine and ten years old, and was molested for all of those years, resulting in an unwanted pregnancy.

Winfrey said, looking around the detention home at all of those girls who had been placed there for being “bad girls,” she remembered having a moment thinking, “now I am officially a bad girl.”

She thought to herself: “I’m now for the rest of my life going to be called a ‘bad girl,’ because I’m going to be put in this place.” She sat there waiting to be processed and said to herself that she did not belong there:

“I don’t even know how this happened to me that I’m in a place for bad girls because I didn’t feel like I was a bad girl.”

Luckily for her, as she sat there thinking, a woman came out and said to her and her mother, Vernita Lee, who died in November 2018, that there was no space for her there and they would have to come back in two weeks.

Young Winfrey and her mom had to leave, and she was released to go and live with her father. According to her, that was her saving grace.

Saving Grace and New Chance
After dodging a bullet from being placed in the detention home, the Mississippi native felt like she had a second chance in life, saying:

“From that moment forward, I felt like I had been somehow saved, that somebody up there recognized that I wasn’t a bad girl.”

“And here I was given another chance, and after I gave birth, at 14 years old to a child who I never even knew how this even happened to me at the time,” Winfrey continued.

She revealed what her father said to her when her baby died at the hospital (born prematurely), giving her a sense of hope after her traumatic experience.

“When that child died, my father said to me, ‘This is your second chance. This is your opportunity to cease this moment and make something of your life,’” the 69-year-old revealed.

After hearing her dad’s words, Winfrey had an epiphany at that moment even though she could not articulate it into words saying, “I took that chance and understood for myself, that now I know better so I can do better.”

Winfrey’s Secret Revealed to The World
Later, the author shared that she had hoped her secret would remain hidden until she could entirely deal with her own deep emotions and feelings.

Winfrey expressed distress after learning that a publication had paid her half-sister, Patricia Lloyd, for the story. She described Llyod as a “drug-dependent, deeply disturbed individual.”

After her pregnancy, the TV personality feared they would expel her from school for being debauched. A few years down the line, she worried that it would damage her thriving career and said:

“I carried the secret into my future, always afraid that if anyone discovered what had happened, they, too, would expel me from their lives.”

Eventually, when her teenage pregnancy story became public knowledge, Winfrey said she was inconsolable and wrote in her essay titled, “My First,” how she reacted to the aftermath:

“I took to my bed and cried for three days. I felt devastated. Wounded. Betrayed. How could this person do this to me.”

Winfrey recalled: “I remember (boyfriend) Stedman (Graham) coming into the bedroom that Sunday afternoon, the room darkened from the closed curtains. Standing before me, looking like he, too, had shed tears, he handed me the tabloid and said, ‘I’m so sorry. You don’t deserve this.’”

Winfrey said she imagined that every single person she came across on the street was going to point their finger at her and scream, saying: “Pregnant at 14, you wicked girl …. expelled!”

However, no one did such a thing to her, and they said nothing, not even strangers or people she knew, and she was stunned by that and later expressed:

“I was shocked. Nobody treated me differently. For 20 years, I had been expecting a reaction that never came.”

Winfrey soon realized that having the secret out in the open was freeing and learned a lot about the shame she felt for keeping it hidden for so long:

“I soon realized that having the secret out was liberating … What I learned for sure was that holding the shame was the greatest burden of all.”

Winfrey’s View on Having Children and Her Daughters
In October 2019, Winfrey opened up about her decision not to have kids in an exclusive interview with People. She revealed that initially, the thought of becoming a mom did cross her mind after she and Graham, whom she met at a charity event in 1986, became engaged:

“At one point in Chicago, I had bought an additional apartment because I was thinking, ‘Well, if we get married, I’m going to need room for children.”

While that never came to be, Winfrey said she saw the kind of responsibility and sacrifice that is needed to be a mother during her years on “The Oprah Winfrey Show,” saying:

“I used to think about this all the time, that I was working these 17-hour days, and so were my producers, and then I go home, and I have my two dogs, and I have Stedman, who’s letting me be who I need to be in the world.”

For that same thought, Winfrey admitted she had no regrets about her choice to have a life without any biological children. “I have not had one regret about that,” she said, adding part of the reason why was because she managed to fulfill it in the way that was best for her, her Academy for Girls.

“Those girls fill that maternal fold that I perhaps would have had. They overfill – I’m overflowed with maternal,” said the proud megastar.

In 2007, the former talk show host realized her five-year dream of creating a safe, educational environment for impoverished girls in South Africa when she opened The Oprah Winfrey Leadership Academy for Girls.

Winfrey lovingly refers to the students as her “daughters,” and they, in turn, respectfully call her “Mom O.” Every Thanksgiving, she invites the first graduating class from the boarding school to her Montecito home for a holiday celebration.

2022 was no different as Oprah once again invited the first graduating class to her home to celebrate the special holiday together. The young woman, who she calls her “daughter-girls,” enjoyed the holiday with her.

Oprah and the first graduating class share many special traditions, one of which is having a welcoming committee for the guests that she will host for Thanksgiving.

In 2022, there was a newcomer on the guest list, one of the woman’s husbands, Paul. As he walked up to the house to celebrate Thanksgiving, he was greeted with an African song.

Oprah said that Thanksgiving was in full swing at her home after posting the video. She then posted a video of her and all her “daughter-girls” before they ate dinner, but there was a twist.

Instead of praying over their food, they sang a song that was sent to them by one of the woman who could not join the, for Thanksgiving that year. As Oprah read the lyrics, the rest of the dinner table sang them.

Once Thanksgiving was over, Oprah ensured that her giving spirit continued. Most are familiar with Oprah’s favorite things list around Christmas and that year she gifted all the women with things from that list.

She posted a video in which she is seen handing boxes to all of the women as they sit around the table. When they opened the gifts their faces were an amalgamation of shock and appreciation.

The women talked excitedly amongst themselves about the gifts they received as the camera panned the table to capture each and every woman’s face.

“The Color Purple” actress once wrote that she and her daughter-girls share lovely meals and even more incredible conversations. Winfrey said it was the definition of what family meant, which is a space to express and be oneself.

In May 2020, Winfrey shared one of the biggest lessons she learned from one of her “daughters,” Sade, who had been living with her and Graham. Sade once told the couple that she needed some time for herself.

Though Winfrey did not initially understand the message, she later realized that it was good for the young lady to have some time alone during quarantine.

She applauded Sade for expressing her needs even though she knew it would hurt their feelings, especially during this time. Despite not having any children, Winfrey has a fulfilling life with her partner and “daughter-girls”