Gypsy Rose Blanchard and Ryan Anderson Dating Timeline

Sparks flew between Gypsy Rose Blanchard and Ryan Anderson after they became pen pals while she was in prison. However, their romance wasn’t meant to be and she announced their split in March 2024. What happened over the course of their relationship timeline leading to their breakup?


Gypsy and Ryan’s love story began in 2020 when he wrote a letter to her while she was serving time at Chillicothe Correctional Center for her involvement in the murder of her mother, Clauddine “Dee Dee” Blanchard.

She received the letter in May 2020, and the pair started exchanging emails and grew close.

“We met in 2020 when the pandemic was really, really strong, and I had a lot of emotional ups and downs because of COVID,” she previously told People about the early stages of their relationship. “Unfortunately, it put the prison in a position to where it restricted our freedom even more … So Ryan has seen me through some really good times, some really hard times.”

July 2021

After communicating for more than one year, the lovebirds finally met in person in July 2021 once the government eased COVID-19 restrictions and Ryan was allowed to visit her in prison.

July 2022

Gypsy and Ryan tied the knot during a ceremony held in the prison on July 21, 2022.

“We do plan on having a reception/redo wedding with all of our family and our friends and the dress and the cake and everything because we deserve that. I deserve that. He deserves that,” Gypsy revealed to People during a 2023 interview. “Our prison wedding was just something to where we can make our vows to each other. It was something that meant something to us. And I think the party is kind of for everybody else and us, but mostly for everybody else.”

December 2023

The couple finally got to live a more conventional life when Gypsy was released from prison on December 28, 2023. Ryan picked her up from the facility, and they began their new lives as husband and wife.

January 2024

Gypsy and Ryan took a major step in their relationship when they adopted a puppy together in January 2024.

“I want to introduce you guys to someone very special,” she announced via Instagram on January 23, 2024. “This is Pixie. She is an eight-week-old baby puppy. She is a sweetheart and she is already spoiled rotten.”

The former inmate then explained that she and Ryan welcomed the pup into their family because they “wanted to get something that [they could] both kind of have to take care of and have as an addition to the family.” Gypsy continued, “We’re not ready to have a baby yet, so this was the next best thing.”

March 2024

One month after adopting Pixie, Gypsy shocked fans when she revealed that she and Ryan split in March 2024.

“People have been asking what is going on in my life,” Gypsy reportedly wrote in a Facebook message on her private profile, according to People. “Unfortunately my husband and I are going through a separation and I moved in with my parents home down the bayou. I have the support of my family and friends to help guide me through this. I am learning to listen to my heart. Right now I need time to let myself find… who I am.”

Raymond Hall/GC Images

April 2024

After Gypsy sparked reconciliation rumors with ex-fiancé Ken Urker in early April 2024, she confirmed that she and Ryan were done for good by filing for divorce on April 8, 2024.

Two days before the filing, Ryan broke his silence on the split on April 6, 2024, and promised fans would learn more about the decision when Gypsy Rose: Life After Lock Up premiered in June 2024.

“I want to thank everybody for the support. It’s been great. I’m just living my life, guys, but you all will see what really happened on Lifetime. We were filming a lot. So, stay tuned for that,” he said in a TikTok video. “I will post more eventually.”

May 2024

Gypsy confirmed that she and Ken were officially back together in April 2024, while she stood by her decision to leave Ryan in a May 2024 interview with People.

“I think that there is a sense of freedom of following your heart, following what you feel like is right for you,” she explained to the outlet. “In my marriage, I felt like a part of me was lost in it, and so I feel like I found that missing piece of myself that I always felt was lost and now reclaiming that back. I definitely feel a sense of belonging in that space.”

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