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Gypsy Rose Blanchard and Ken Urker’s Relationship Timeline: From Pen Pals to Engagement

Gypsy Blanchard and Ken Urkers Relationship Timeline
Gypsy Blanchard and Ken Urker Splash news/MEGA

Gypsy Rose Blanchard and Ken Urker began their relationship as pen pals.

Following the 2017 HBO documentary Mommy Dead and Dearest, Urker wrote Blanchard a “letter of support” while she was incarcerated. The twosome kept in touch while Blanchard served her prison sentence and eventually shared a smooch when he visited her in jail. (She spent seven years in prison for her role in the 2015 murder of her mom, Clauddine “Dee Dee” Blanchard.)

“He came and it was kind of a funny story but within the first 30 minutes he leaned over and gave me the most wonderful kiss of my whole life,” she recalled to E! News in 2019. “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.'”

Urker popped the question in October 2018 while Gypsy was still behind bars, however, the twosome went their separate ways the following year. Gypsy subsequently wed Ryan Scott Anderson in 2022 during a prison ceremony, but she filed for divorce after less than two years of marriage.

In April 2024, Gypsy confirmed that she and Urker had rekindled their romance.

Scroll down to see Gypsy and Urker’s relationship from the beginning:

Gypsy Blanchard and Ken Urkers Relationship Timeline
Splash news/MEGA


After Urker initially wrote Gypsy, the pair continued to correspond. The duo ultimately met when he visited her in prison and they shared a kiss.

October 2018

Urker proposed to Gypsy during a prison visit — and she said yes.

“We bounced around the idea, we have a pretty solid thing going and we’re pretty sure this is what we want,” she told E! News in 2019. “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.”

Urker gave Gypsy a silver band, which she said got confiscated, but he later bought her a new one.

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August 2019

Gypsy opened up about the couple’s desire to have children. “We’re probably not going to wait a year or two after I am out,” she told E! News in August 2019. “We want to give ourselves that adjustment period, that way we can have our big wedding ceremony, have a honeymoon, have time together as just us, and then work on having a family after that.”

As for how many kids Gypsy wanted to have, she said, “probably two or three.” She added, “My mother didn’t allow me to have a relationship with my half-siblings, so growing up as an only child, I would want my child to have a sibling and to have that bond.”

Gypsy noted that the twosome don’t fight, but instead, talk out their problems. “He’s very understanding, very supportive, very easy to talk things out with. He’s not one of those people who is going to be like, ‘Well, this is your fault,’” she said. “He’s very sensitive to my emotions, especially because I’m in prison, my emotions are a little bit heightened with me.”

That same month, news broke that Gypsy and Urker had gone their separate ways. While they later reunited, their romance was short-lived. By June 2022, Gypsy had married Anderson.

Gypsy Blanchard and Ken Urkers Relationship Timeline
Splash news/MEGA

June 2022

Two weeks before Gypsy walked down the aisle with Anderson, she made a phone call to Urker.

“I called Ken two weeks before I got married,” she exclusively recalled to Us Weekly in May 2024. “Ken has consistently been brought up in a way that I can never let go of my feelings, but I put them on the back burner to do what was best for my marriage. And so, having that be a point of contention has been a thread throughout, but I didn’t leave Ryan for Ken. That was just sort of a realization [of], ‘Hey, we still love each other after the fact.’”

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April 2024

Days after announcing her split from Anderson, Gypsy got matching husky tattoos with Urker. Urker’s mom, Raina Williams, told People that the twosome were “not back together” and that Urker was “just being a supportive friend.”

“I think she’s a sweet girl,” Williams said in April 2024. “I think she’s made her mistakes and she’s trying to learn from them like anyone else. And I care a lot for Gypsy and I want to see good things happen for her.”

Later that month, Gypsy confirmed that she and Urker 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 told TMZ. “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.”

The outlet also obtained photos of Gypsy and Urker kissing and holding hands at the New Orleans Jazz & Heritage Festival.

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May 2024

Gypsy shared her and Urker’s plans to alter their living situation. “He’s actually going to be moving to Louisiana to be closer to me,” she told Entertainment Tonight in May 2024.

She also noted that she wouldn’t be opposed to saying “I do” again. “I’ve always said Ken was my soulmate. But I don’t want to move too fast because, you know, I want to pace myself,” she said. “I don’t want to put expectations and make things too heavy. We’re just basically enjoying our time together and, you know, hopeful for what the future has.”

June 2024

In her first YouTube video, Gypsy gushed about her relationship with Urker while replying to a fan question which asked, “What is the first thing you did when you gained your independence that made you feel the happiest?” She answered by stating her choice to pursue her and Urker’s romance after her divorce from Anderson brought her the most joy.

“I felt like I made that choice as a free woman. I made that choice as an independent woman, and I think everyone should follow their heart. If they know what they want in life and they know what’s gonna make them happy, I absolutely feel like no matter what, you should go for it,” she explained. “Life is too dang short to be sad or feel trapped by anything in your life. I was in a marriage that I was unhappy with and I knew that my heart was elsewhere, and so, I followed that. And I’m happy, I’m very happy. This is the happiest that I’ve ever been in my entire life, and I’m not ashamed of that.”

Gypsy Rose and Ken Relationship Timeline
Courtesy of Gypsy-Rose Blanchard/Instagram

July 2024

Gypsy announced that she and Urker were expecting their first baby together in an emotional YouTube video.

“I know the rumors have been flying around for quite some time now, and I’m happy to announce that I am 11 weeks pregnant. Ken and I are expecting our very first child come January 2025,” Gypsy said at the time, adding that the pregnancy was “not planned.”

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