“We were holding the same photo from Google!” JoJo Siwa couldn’t quite believe what happened when she and boyfriend Chris Hughes compared ideas for her dream engagement ring.
The singer and dancer, 23, shared the story with People at the Industry Dance Awards on October 21, that took place at Avalon Hollywood in Los Angeles.
Siwa and Hughes, 33, have not announced an engagement. Her account concerned a possible future proposal.
Asked how their relationship was going, Siwa described their time together as “lovely.” She said they were approaching their year-and-a-half anniversary.
Siwa Wanted Hughes to Choose the Ring Himself
Siwa had already given her mother an instruction. If Hughes ever asked what sort of ring she would want, he should be encouraged to design it himself. She had nevertheless found her own favorite while browsing online, a photograph that captured her ideal design.
During dinner one evening, she asked Hughes what he thought her dream ring would look like. They agreed to reveal their choices on the count of three, without showing each other beforehand. The photograph featured a blue, emerald-shaped stone.
Her Christmas Ring Sometimes Moves to Her Wedding Finger
The following evening, Siwa attended Dancers Against Cancer’s Gala of the Stars with Hughes at the Beverly Hilton. Speaking to E! News, she revealed a habit he hadn’t known about.
Hughes had given her a ring for Christmas in 2025, which she said she wore every day. Although it was on her right hand during the interview, she sometimes moved it to her left to see how it felt on her wedding finger.
Hughes smiled at the admission and called it “kind of cute.” Siwa said she occasionally forgot to move it back, then worried that someone would photograph her and assume she was engaged.
Asked about marriage, Hughes said he hoped to have a wedding and family someday, but was taking things one step at a time. Siwa said they were happy with their lives as they were.
She also performed “Boomerang” at the gala. Ahead of the performance, Hughes praised her work and said she made him proud every day.
Siwa Once Imagined a Much Simpler Wedding
Hughes explained the family influence on his outlook in a July 23, 2025, interview with Us Weekly. He said he and Siwa had grown up in loving households and wanted to carry that experience into parenthood.
Siwa explained how her own expectations had changed during a September 9, 2025, appearance on Reign with Josh Smith. She had once imagined signing paperwork or going to Las Vegas, without wanting a full wedding celebration.
As People reported from the podcast interview, dating Hughes had her picturing her father walking her down the aisle and a first dance with her husband.
By December, they were teasing each other about who might propose. In a joint interview with The Sun’s Fabulous, Hughes said he preferred an unexpected moment. Siwa joked that if he waited seven years, she would get down on one knee herself.
Their Reality Show Friendship Became a Long-Distance Romance
Siwa and Hughes met while competing on Celebrity Big Brother UK in April 2025. Hughes had previously appeared on Love Island. They initially described their bond as a friendship, with Siwa publicly confirming their romance that June.
Living on opposite sides of the Atlantic required regular travel. Hughes told Us Weekly in his July interview that they had not spent more than two weeks apart since leaving the house, using breaks in their schedules to visit each other.
The relationship also inspired her song “Serendipity.” At the March 23, 2026, premiere of the Hannah Montana 20th Anniversary Special, she told People that the title reflected the unexpected way their lives had connected.
On May 27, they marked their first anniversary with Instagram tributes. Siwa thanked Hughes for their phone calls, flights and memories together.