Gypsy Rose Blanchard’s Relationship With Ex Ryan Anderson Reaches a Boiling Point in Docuseries Trailer

In a first look at Gypsy Rose: Life After Lockup, tensions build between Gypsy Rose Blanchard and her ex Ryan Anderson over conversations about Ken Urker.

By Olivia Evans May 29, 2024 1:14 PM
| Updated May 29, 2024 1:13 PM
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Gypsy Rose Blanchard and Ryan Anderson are sharing what led to their split. 

The upcoming Lifetime docuseries Gypsy Rose: Life After Lockup will explore the 32-year-old's unraveling relationship with her estranged husband, as well as her recent rekindling with her ex fiancé Ken Urker since her December 2023 release from prison. 

The new trailer, released May 28, teases that Gypsy's relationships will be a big part of her upcoming docuseries, as it opens with her asking Ryan, "Are you happy?"

To which the 37-year-old replies, "I'm very happy."

"I just think that I would be happier," Gypsy posits, "somewhere else."

And tensions come to a head when Ryan alludes to what is to come—especially when it comes to Gypsy reconnecting with her ex. 

"Oh, go call Ken," he tells her. "You're probably already talking to him anyway."

The comment leads Gypsy to tears—but eventually Ken is seen coming back into the picture, which doesn't go over so well.

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Gypsy Rose Blanchard's Photos With Husband Ryan Anderson

As Ryan later puts it, "He's trying to weasel his way back in now that Gypsy is out of prison."

However, Gypsy also opened up about simply growing apart from her ex—even without Ken in the equation. 

"I don't like being controlled," Gypsy says at one point, before later adding, "I want a divorce."

The latest glimpse at the former couple's relationship comes a little over a month after Gypsy filed for divorce from her ex in April. Shortly thereafter, the 32-year-old officially rekindled her romance with Ken.

Jamie McCarthy/Getty Images

"We realized that our love for each other is simply undeniable," Gypsy told TMZ at the time, "and life is too short to not take a chance." 

Meanwhile, Ryan maintains he was blindsided by Gypsy's filing. 

"I'm not doing well with it," he told the Daily Mail in April. "For me it just came out of the blue. I had no idea she still had such strong feelings for him."

In addition to exploring the behind-the-scenes of Gypsy's relationships, the series will also detail her learning how to be an adult after serving seven years in prison for involvement in the murder of her mother Claudine "Dee Dee" Blanchard

Fans will be able to learn Gypsy's full story when the Lifetime series drops June 3. In the meantime, keep reading to see what she has shared so far in her life of freedom. 

"First Selfie of Freedom!"

After being released from prison on Dec. 28, 2023, Gypsy Rose Blanchard snapped her first Instagram selfie.

"Married Life"

Gypsy and then-husband Ryan Anderson shared a glimpse into their new era together.

"Sister Love"

Gypsy reunited with her sister Mia Blanchard amid her new chapter.

Goodbye 2023

"A New Years Eve Eve kiss with my hubby."

Turning the Page

Gypsy also ended 2023 with an Instagram selfie.

Red Carpet Debut

Gypsy and Ryan walked their first red carpet in January 2024 at the premiere of her Lifetime docuseries The Prison Confessions of Gypsy Rose Blanchard.

PDA Alert

Gypsy and Ryan kissed on the red carpet at the premiere.

Breakup

In late March 2024, three months after her prison release, Gypsy shared that she and Ryan broke up.

"People have been asking what is going on in my life," she wrote in a statement on her private Facebook page, according to People. "Unfortunately my husband and I are going through a separation and I moved in with my parents home down the bayou."

Physical Transformation

Gypsy underwent a rhinopasty and septoplasty (nose job) April 5, 2024. Her physical transformation will be documented on Lifetime's Gypsy Rose: Life After Lock Up.

Divorce

Gypsy filed for divorce from Ryan on April 8, 2024, according to court documents obtained by TMZ. The filing came nearly two years after their July 2022 prison wedding.

Gypsy's Tribute to Her "Soulmate"

In late April 2024, weeks after filing for divorce, Gypsy announced she got back together with ex-fiancé Ken Urker. The following month, she made their rekindled romance social media official by sharing a video montage of their romantic moments on TikTok.

Love Story

In her video, Gypsy described her love story with Ken as "legendary."

The Burning Question

And when a fan, using her own past comments about ex Ryan, took the oppotunity to ask her in the comments a NSFW question about Ken, Gypsy responded quickly and candidly.

Animal Style

Gypsy tried her first In-N-Out Burger, a Double-Double burger served animal-style. She rated it a 7.

Catching Up With a Kardashian

Gypsy called getting to meet Kim Kardashian, who has become a criminal justice advocate in recent years, a "huge honor."

"She's a really sweet woman and I really appreciate her taking the time to talk with me," Gypsy told E! News host Keltie Knight. "We had a lot to talk about as far as prison reform goes. I know that she's done some really amazing things with prison reform. And that's really close to my heart because I've been on that side of the fence."

Oh Baby

Less than three months after filing for divorce, Gypsy announced that she and her new boyfriend Ken were expecting their first baby together. 

"I'm happy to announce that I am 11 weeks pregnant," she shared in a July 2024 YouTube video. "This was not planned at all, it was completely unexpected."

Body Art

Gypsy showed off her meaningful new tattoos in July.

It's a Girl

Gypsy and Ken celebrated at a sex reveal party for their first baby in August 2024 and, at a baby shower in November, shared that they'll be naming her Aurora Raina Urker.

Harrowing Memoir Details

With co-authors Melissa Moore and Michele Matrisciani, Gypsy told her dramatic life story to date in her book My Time to Stand, which came out in December.

She's a Mom

Gypsy gave birth to her first baby on Dec. 28, 2024, exactly one year after her prison release.

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