We’re living in a beautifully messy era. Taylor Swift wrote a double album about a short-lived rebound with Matty Healy. Tashi Duncan and her two “little white boys” have people fantasizing about love triangles and throuples. And now, Gypsy Rose Blanchard is making sure the whole world knows that she’s back together with her ex-fiancé, Ken Urker. This official rekindling notably comes about a month after her split from Ryan “The D Is Fire” Scott Anderson. Honestly, I’m so here for her living her best reality star life. (Gypsy has an upcoming docuseries about her post-prison adventures called Gypsy Rose: Life After Lock Up.)
Those of us who follow Gypsy closely are aware of the extensive Ken and Gypsy romantic history. These lovebirds go back seven years, and Gypsy’s lingering strong feelings for him actually caused issues between her and Ryan ahead of their wedding. Can you really blame a girl for embracing the Kenergy? Just so everyone understands the gravity of this reconciliation, here’s an extremely detailed timeline of Gypsy and Ken’s juicy on-and-off relationship.
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2017: Ken writes to Gypsy after watching Mommy Dead and Dearest
The star-crossed lovers started chatting Ken reached out to Gypsy upon watching Mommy Dead and Dearest, the May 16, 2017 documentary about her. Gypsy told E! that Ken wrote her a “letter of support” and they quickly became pen pals and buds. “It was pretty soon after that that we started talking on the phone,” she said. “We would spend hours on the phone. I talked to him like I had known him my whole life and vice versa.” A soul connection!
October 2018 – Ken proposes to Gypsy
During one special visit to the Chillicothe Correctional Facility, Ken asked Gypsy to marry him. She explained to E! that they’d been talking about tying the knot for a while. “We bounced around the idea, we have a pretty solid thing going and we’re pretty sure this is what we want,” she recalled. “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.”
August 2019: They split then get back together
They split briefly but reunited soon after that. Obviously, things didn’t end up working out that time either.
Summer 2022: Gypsy and Ken are chatting weeks before her wedding to Ryan Scott Anderson
After Ken, Gypsy fell for another guy who wrote her letters to prison: Ryan Scott Anderson, the Louisiana teacher we’re probably all quite familiar with by now. However, Gypsy low-key continued to hold a flame for her ex. She confessed her remaining feelings for Ken to Ryan just a few weeks before they were set to tie the knot. Our girl was still secretly talking to Ken and even had a dream about leaving Ryan for him. Messyyyyy. Siri, play “Guilty As Sin?” by Taylor Swift.
August 2022: Gypsy gets married to Ryan
The now-exes worked through their Ken issues and exchanged vows in August 2022.
March 28, 2024: Gypsy and Ryan split
Sadly, the D just wasn’t fire enough. Gypsy wrote on Facebook: “People have been asking what is going on in my life. Unfortunately my husband and I are going through a separation and I moved in with my parents home down the bayou.” She noted that she’s focused on self-discovery. “Right now I need time to let myself find… who I am,” Gypsy added. Yesss, just a single lady getting to know herself (with Ken).
April 2, 2024: Gypsy and Ken get lunch and matching tattoos days after her Ryan breakup
My queen didn’t waste any time after splitting from Ryan. Five days after that announcement, she and Ken linked to grab lunch and get matching husky dog tattoos. It’s so unhinged, you have to admire it. At the time, Ken’s mother claimed that they were not back together, just friendly. Hmmm.
April 29, 2024: There’s a photo of Gypsy and Ken making out
Gyspy is really going hard to promote Gypsy Rose: Life After Lock Up. She sent TMZ a photo of herself and Ken mid-kiss. Apparently, they went to the New Orleans Jazz & Heritage Festival over the weekend and were very publicly affectionate. Well, well, well. It’s fine ’cause I support women’s wrongs.
July 9, 2024: Gypsy and Ken are expecting their first child
On July 9, Gyspy took to Instagram to announce that she and Ken are expecting a baby!
“I’m happy to announce that I am 11 weeks pregnant,” Gypsy said in her announcement video. “Ken and I are expecting our very first child… We’re both very excited. This was NOT planned at all. It was completely unexpected.” I’m quaking. She added that they’re both “very excited to take on this new journey of parenthood” and noted that she wants to give her child “all of the things I wished I could’ve had when I was little.”
