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January 30, 2026

More than two years after Graziadei got down on one knee during "The Bachelor," he found a quieter way to ask Anderson the same life-changing question again.
The couple, who first got engaged during the season 28 finale of "The Bachelor," recently celebrated another proposal in Cabo San Lucas. This time, the moment was private, personal, and entirely their own.

Joey Graziadei and Kelsey Anderson at HGTV's event to celebrate "Bachelor Mansion Takeover" at The Bachelor Mansion on March 12, 2026, in Los Angeles, California. | Source: Getty Images
Joey Graziadei, 31, and Kelsey Anderson, 28, shared the exciting news of their second engagement in a joint Instagram post, where the former Bachelor kept the announcement simple and joyful. "SHE SAID YES (again)," he wrote.

Joey Graziadei and Kelsey Anderson celebrated their second engagement in Cabo San Lucas in a post shared on May 26, 2026. | Source: Instagram/joeygraziadei
In his caption, Graziadei explained that the second proposal was not about replacing their first engagement. Instead, it was about giving their relationship a moment that belonged only to them. He shared:
"Proposing again meant taking something that was already extraordinary and making it fully our own."

Joey Graziadei and Kelsey Anderson shared a kiss during their second engagement celebration in Cabo San Lucas in a post dated May 26, 2026. | Source: Instagram/joeygraziadei
He added that it meant everything to reaffirm their love and promise to each other "just the two of us," before writing, "Forever isn't enough with you. I cannot wait to make you my wife."
The renewed engagement came as the pair continued planning their 2027 wedding, a celebration they have already decided will reflect their relationship more than their public image.
In April, Anderson opened up about their wedding plans during an appearance on Brianna "Chickenfry" LaPaglia's "PlanBri Uncut" podcast. Despite their Bachelor Nation fame, she said the couple made one clear decision early in the planning process: Their wedding would not become a sponsored event.
"We don't want to do any brand deals for our wedding," Anderson said. She explained that she did not want to feel obligated to post about sponsored parts of the day, including anything like a branded bar or other promotional arrangement.

Kelsey Anderson discussed her and Joey Graziadei's wedding plans during a "PlanBri Uncut" podcast episode posted on April 12, 2026. | Source: YouTube/Plan Bri Uncut
Graziadei and Anderson have already brought in wedding planners Josiah Carr and Justin McGregor of SAMKOMA to help shape the big day.
"We just want it to be able to be seamless and about us," she explained. Still, Anderson said she and Graziadei plan to hire wedding content creators to help document the celebration.

Kelsey Anderson opened up about wanting a romantic and intimate wedding celebration during her appearance on the "PlanBri Uncut" podcast. | Source: YouTube/Plan Bri Uncut
The difference, she explained, is that she does not want to be the one working during her own wedding. "But I'm not gonna be making TikToks," she said. "They'll be making the TikToks so I don't have to worry about it, and I can just be in the moment."
As for the look and feel of the wedding, Anderson revealed that they are leaning toward something "romantic" and "moody," with candles and possibly a "garden party vibe" during cocktail hour.

Brianna "Chickenfry" LaPaglia and Kelsey Anderson discussed wedding planning and social media during an episode of the "PlanBri Uncut" podcast. | Source: YouTube/Plan Bri Uncut
Even so, she is not trying to control every detail. "I'm not 100% set on anything," she shared, adding that she expects to be "very go with the flow."
For Anderson, the essentials are simple: Graziadei, good music, and the people they love. "As long as he's there, I'm there, we've got a good DJ, a good band, I feel like I'm pretty set," she said.
Graziadei and Anderson have already brought in wedding planners Josiah Carr and Justin McGregor of SAMKOMA to help shape the big day. The planners previously described the couple as "two of the sweetest humans" and said they felt fortunate to work with them.
Graziadei has also started forming his wedding party. Earlier this year, he revealed that fellow Bachelor Nation alum Tanner Courtad would serve as his best man.
The couple first met on Graziadei's season of "The Bachelor," after he appeared on "The Bachelorette." During the March 2024 finale, he proposed to Anderson, ending the season with their engagement.
After the finale aired, the pair spoke about adjusting to life together after keeping their relationship private while the show was on television. Anderson said they kept a shared note filled with simple things they wanted to do as a couple, from dance classes and pottery classes to grocery shopping.

Joey Graziadei and Kelsey Anderson at Hulu's Get Real House event at Casa Lago on April 22, 2026, in Beverly Hills, California. | Source: Getty Images
They also attended couples therapy to strengthen their communication during the unusual start to their relationship. Graziadei said at the time:
"It's definitely not easy because we both do appreciate the physical touch. But the couples' counseling made a huge difference for us."
Now, with a second proposal and a 2027 wedding ahead, Graziadei and Anderson appear to be making each milestone their own.