9 Famous Men Who Got 2 Women Pregnant At Once

Read on to find out how these stars handled multiple pregnancies at once…

1. Jimmie Allen

Jimmie Allen recently welcomed three children with two different women -- leaving fans with a lot of questions. He set the record straight on his YouTube channel, explaining that he welcomed a set of twins with his longtime friend Danielle in the summer of 2023 and his wife Alexis gave birth to a son a few months later. He clarified that he was separated from Alexis at the time Danielle got pregnant but they later decided to give their relationship another shot.

“[The twins have a] different mother -- my friend Danielle. I’ve known Danielle for years. Way before I became ‘Jimmie Allen.’ And at the time that she got pregnant with the twins, I wasn’t with Lexi, and [Danielle] wasn’t with her husband,” Jimmie explained.

During the interview, Jimmie also admitted to cheating on Alexis on multiple occasions and that he doesn’t believe he’s ready for marriage. The couple have once again called it quits.

2. Billy Ray Cyrus

Early in his career, Billy Ray Cyrus became a dad to two children just months apart. Shortly after separating from his first wife, Billy Ray met a woman named Kristin Luckey. According to People, during their brief romance, Kristin became pregnant. While she was expecting, the couple went their separate ways and Billy Ray began a romance with his now ex-wife Tish Cyrus. It wasn’t long before Tish also became pregnant.

In April 1992, Kristin gave birth to a son named Christopher and in November, Tish gave birth to their daughter Miley.

“I love this baby son. His mother and I are friends. I respect her, she respects me, and we created a beautiful baby together,” Billy Ray told People shortly after Christopher’s birth.

3. Tristan Thompson

Tristan Thompson found himself in the middle of a cheating scandal when it was revealed that he had a baby with his mistress Maralee Nichols in December 2021. Just weeks before the baby’s birth, Tristan had encouraged his then-girlfriend Khloé Kardashian to move forward with a surrogate to carry their second child. By the time Khloé had learned about the other child, the surrogate was already pregnant. Shortly after, Tristan issued a public apology to Khloé.

“I sincerely apologize to everyone I’ve hurt or disappointed throughout this ordeal both publicly and privately. Khloé, you don’t deserve this. You don’t deserve the heartache and humiliation I have caused you. You don’t deserve the way I have treated you over the years,” he wrote. “My actions certainly have not lined up with the way I view you. I have the utmost respect and love for you. Regardless of what you may think. Again, I am so incredibly sorry.”

Khloé and Tristan’s second child was born in July 2022. They have not reconciled their relationship.

4. Arnold Schwarzenegger

Arnold Schwarzenegger’s ex-wife Maria Shriver became pregnant with the couple’s fourth child at almost the same exact time that Arnold slept with the family’s housekeeper, Mildred Baena. Maria welcomed Christopher on September 27, 1997 and just five days later, Mildred gave birth to a boy named Joseph. Arnold later claimed that he had no idea that he was Joseph’s father until the little boy started to look like him.

After discovering Joseph was his son, he decided to continue to employ Mildred and provided her with extra wages to care for their child. Maria did not figure out that Joseph was Arnold’s son for a number of years, finally confronting him during a therapy session shortly after he ended his run as governor of California.

“I thought my heart stopped, and then I told the truth. ‘Yes, Maria, Joseph is my son.’ She was crushed because of that. I had an affair in ’96. In the beginning I really didn’t know. I just started feeling the older he got the more it became clear to me,” he said in the Netflix docuseries Arnold.

He continued, “I am going to have to live with it the rest of my life. People will remember my successes and they will also remember my failures. This is a major failure. I had failures in the past in my career, but this is a whole different ball game…It was wrong what I did. But I don’t want to make Joseph feel that he is not welcomed in this world -- because he is very much welcomed in this world. I love him and he has turned out to be an extraordinary young man.”

5. Nick Cannon

Nick Cannon has become known for his ever-expanding family, welcoming 12 children with six different women over the course of the past decade. While the mothers of his children all seem to be in support of Nick’s unique family structure, there’s been more than one occasion when his baby mamas have been pregnant at the time. While it may be an overwhelming situation for most people, Nick says he loves being a dad.

“Every day I just wake up excited as a father,” he told People. “I’m so excited about all my kids. Constantly, from every aspect of it. From them getting citizen of the month awards in the first grade to the birth of the new ones.”

6. Hugh Grant

Hugh Grant is now the proud dad to five kids -- and two of those children were born just months apart. While it wasn’t made public at the time, Hugh’s now-wife Anna Eberstein secretly gave birth to a son named John in September 2012. Then, just three months later, his former girlfriend Tinglan Hong gave birth to her second child with Hugh, a son named Felix. Hugh has never spoken out about welcoming the two children so close together.

7. Diddy

Back in the early 2000s, Diddy made headlines when he got two women pregnant at the same time. Towards the end of 2005, Sarah Chapman became pregnant with his child and several months later, his on-and-off girlfriend Kim Porter learned she was expecting twins. In July 2006, Sarah gave birth to a daughter and in December, the twins were born.

While Kim says she was pregnant when a friend told her that Diddy had fathered another child, she says he didn’t personally inform her about the baby until after she gave birth.

“He told me that he may have gotten himself into a situation and he may have fathered another child outside the relationship and I said, ‘Really? Well, I already knew. I’m glad you decided to be a man,’” she said, per People. “I was like, ‘Dude, this is so wack I can’t even respect you right now.’ And for me, once the respect is gone, I’m not even listening to you.”

8. Lil Wayne

In 2009, Lil Wayne learned that he was expecting babies with two women at the same time. At the time, he was engaged to singer Nivea and on the day her pregnancy was confirmed, she discovered that Lauren London was also expecting a child with the rapper. While Nivea says she was upset by the news, it actually helped her foster a friendship with London.

“It was very crushing, then she and I became very close, ironically, after he and I decided to let it go. She was a real good friend to me during my mother’s death. I know that sounds weird, but we were two people going through something that was along the lines of humiliating. It felt like, who else could you share this oddly unique situation with?” she told VLADTV.

She continued, “We called each other to get information because she and I were both previous relationships of his in our younger years as well. But it was our first time ever talking. We talked about all kinds of stuff from the past and in that we connected as friends. It’s still a testament to the type of man he is because all of his baby mothers, we’re all cool with each other. We get now that the children are here, damn it! They're here now. You can't take nothing back. So we are the best mothers that I’ve ever seen in a group with the same baby father. I think it's amazing.”

9. Elon Musk

Elon Musk is the father of 11 children and three of those kids were born just a few months apart. In November 2021, Elon and Shivon Zilis, the project director at his Neuralink company, secretly welcomed a set of twins, a boy named Strider and a daughter Azure. Meanwhile, a surrogate had been pregnant with Elon’s second child with Grimes. Just a month after the twin’s birth, the surrogate gave birth to a little girl that they named Exa Dark Sideræl.