Gypsy Rose Blanchard and Ken Urker's Relationship Timeline: From First Meeting to His Death

Gypsy Rose Blanchard and Ken Urker had a complicated romantic history.

The Gypsy Rose: Life After Lock Up star dated Urker on and off from 2017 to 2019 and again from 2024 to 2026. They first became romantically involved after her relationship with Nicholas Godejohn and before she married Ryan Anderson. Years later, after Blanchard and Anderson separated, she and Urker found their way back to each other and rekindled their romance.

Scroll down for a closer look at Blanchard and Urker's tumultuous relationship, from their early romance and reconciliations to the events leading up to his death.

The pair first connected in 2017 when Urker contacted Blanchard after watching Mommy Dead and Dearest. The HBO documentary examined the abuse she said she endured at the hands of her mother, Clauddine "Dee Dee" Blanchard, and the events surrounding Dee Dee's 2015 murder.

"We became fast friends," Gypsy Rose told E! News in 2019 when asked how she and Ken met. "It was pretty soon after that that we started talking on the phone. We would spend hours on the phone. I talked to him like I had known him my whole life and vice versa."

After weeks of exchanging letters, Gypsy Rose sent Ken a visitation form so he could visit her in prison. Within the first 30 minutes of their meeting, Ken reportedly leaned over and kissed her.

"So it's a prison visitation room, so the level of physical contact that is allowed is limited to holding hands and a brief hug, and a closed mouth kiss. The kiss he gave me was quite passionate. I looked at him and was like, 'I didn't even know you liked me like that', and he said 'Yeah, I have for a while'. And I'm like, ‘I have for a while too,'" she recalled in the 2019 interview.

Gypsy Rose and Ken took their relationship to the next level when he proposed to her during one of his visits to Chillicothe Correctional Center in October 2018.

According to the former inmate, they had already discussed marriage before Ken popped the question with a silver band that was later confiscated while Gypsy Rose was in prison.

"So, on the October visit he held my hands close and told me how much I meant to him and he's like, 'I would really, really be honored if I could have your hand in marriage,' and I said yes," she revealed to E! News.

The engagement remained private until Gypsy Rose publicly confirmed it the following year.

In August 2019, Gypsy Rose and Ken called it quits less than a year after their engagement.

"There were many adults in his life, presumably much 'wiser' than he, who suggested it wasn't the right time for me to be married," she disclosed in her 2024 book, My Time to Stand.

She wrote, "'If you love her, you'll set her free,' was the common piece of advice he'd hear again and again, sometimes from prominent Hollywood therapists and other media personalities — sometimes from those in my own immediate family. I see now, he believed he was acting in my best interest by sacrificing his own needs and wants."

They briefly reconciled later that month, but their reunion proved short-lived. Gypsy Rose later moved on and married Ryan.

After Gypsy Rose filed for divorce from Ryan, she was photographed holding hands with Ken and later debuted matching tattoos.

She also confirmed to TMZ that they had rekindled their relationship.

"After reconnecting earlier this month, we realized that our love for each other is simply undeniable, and life is too short to not take a chance," she said. "We have a history that made for the perfect foundation for a new beginning. We are together and in a wonderful place in our relationship. We know it is going to be a long road ahead but are excited for the future."

In a YouTube video titled "I'm Pregnant, My Journey So Far," Gypsy Rose announced her pregnancy and named Ken as the baby daddy.

"We're both very excited. This was not planned at all. It was completely unexpected," she said in the video.

Gypsy Rose and Ken welcomed their daughter, Aurora Raina Urker, in December 2024.

In the months that followed, Gypsy Rose publicly expressed confidence in her future with Ken. She also revealed they had begun therapy to work on their relationship.

In a TikTok live after Ken's death, his sister, Autumn Urker, said the couple had "split up" before his passing.

Ken was found dead at his home in Raceland, Louisiana, on October 1 — his 34th birthday. Gypsy Rose said she believed he may have died from an overdose, but an official cause of death had not yet been determined.

Gypsy Rose shared an emotional tribute to Ken, remembering him as an "amazing father," her "soulmate" and her "greatest love story."

"Ken loved our daughter," she continued. "She is a beautiful reflection of his enduring spirit, and through her, a part of him will always remain with us. I will make sure she grows up knowing how deeply her father loved her and who he was beyond what strangers on the internet chose to say about him."