From being engulfed by “hurricane-like winds” and facing last-minute outfit drama to getting locked out of the reception and having his mom Mechele pulled over by cops en route to the ceremony, there was no shortage of hurdles on O-Town singer Jacob Underwood’s wedding day.

But as he stood atop picturesque Sunset Cliffs in San Diego, he forgot about any curveballs when his dazzling bride Chandler Underwood (nee Bay) walked towards him with the 15-foot veil of her gorgeous lace gown billowing behind her.

“She looked incredible,” the 41-year-old boy bander gushes to us, a day after returning from his Mexican honeymoon. “Because of the crazy winds, her veil was floating behind her 20 feet in the air, with rays of sunshine peeking through as the clouds changed colours. It was the most stunning sight I’ve ever seen.”

Jacob and Chandler Underwood. Credit: Tara Sweeney
Jacob and Chandler Underwood. Credit: Tara Sweeney

While Chandler, 31, admits such forceful gusts weren’t ideal for her blond locks, the winds accentuated the exquisite bridal outfit by Australian label Grace Loves Lace.

But it’s another special lady who stole the show before Chandler’s arrival – the couple’s three-year-old daughter and flower girl Everest, who had been practising scattering petals ahead of the big day. The cutie, who wore a dress from David’s Bridal, even insisted it was her own wedding!

“Every time I told her mommy and daddy were getting married, she’d go, ‘Evie and mommy are marrying daddy. Daddy’s gonna be our husband,’” Chandler shares.

Jacob and Chandler Underwood. Credit: Tara Sweeney
Jacob and Chandler Underwood. Credit: Tara Sweeney

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Adds Jacob: “She kept saying, ‘Daddy, you’re gonna marry me and mommy.’ It was so cute! Then when we left for our honeymoon, we told her we’ll bring her a gift and she goes, ‘I want a ring like mommy’s with diamonds. I didn’t get one.’”

Chandler was pregnant with Everest in 2018 when Jacob proposed with the help of his O-Town bandmates at the Eiffel Tower in Paris. The couple met in 2016 after Jacob caught Chandler (a musician who released a heartwarming single inspired by her pregnancy, ‘I See You’ in 2018, but is now happily focused on motherhood) performing at a Nashville bar and signed on to manage her.

Jacob and Chandler Underwood. Credit: Tara Sweeney
Jacob and Chandler Underwood. Credit: Tara Sweeney
Jacob and Chandler Underwood. Credit: Tara Sweeney
Jacob and Chandler Underwood. Credit: Tara Sweeney

Following two pandemic-fuelled wedding postponements, the San Diego-based couple decided to hold a smaller ceremony at their favourite hiking and diving spot on New Year’s Eve.

Given the extended engagement, Chandler spent the morning “in shock” the wedding was finally going ahead, while Jacob hung with his brother Bryan and bandmate Trevor Penick (also the celebrant) watching football and drinking champagne before realizing his wedding shoes were two different sizes. “Luckily, I had some Gucci shoes as a backup!” he says.

Although the shoe crisis was diverted, there was another hitch: Jacob’s family (Mechele, Bryan and his wife Sarah, and sister Danielle and her husband Kyler) were pulled over, thanks to their limousine missing its rear licence plate.
“Everyone was sitting in freezing wind on the cliffs waiting for them to get there,” laughs Chandler, one of eight siblings, who was walked down the aisle by her younger brother Sonny to the Piano Guys’ version of Coldplay’s “A Sky Full of Stars”.

“By the time I walked down the aisle, apart from worrying about my hair and feeling like I was about to take flight, I couldn’t get over the fact he was still standing there!”

Jacob and Chandler Underwood. Credit: Tara Sweeney
Jacob and Chandler Underwood. Credit: Tara Sweeney

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Wearing a Boss suit, Jacob was thrilled to have Trevor by his side officiating the ceremony, while O-Town’s Dan Miller was also present (fourth member Erik-Michael Estrada was unable to attend after being exposed to COVID-19 shortly before the nuptials). The “All Or Nothing” singers recently celebrated 20 years since they formed their group on reality series “Making the Band”.

“There’s nobody else we’d have officiate than Trevor,” says Jacob. “We travel with Trevor as our third wheel all the time! He’s best friends with both of us and always there to give advice and encourage our relationship. For somebody who shares the history of our relationship to stand there and vouch for us was so special.”

“He joked how when we first started talking, Chandler wanted me to manage her and I told her I’d rather date her. He let everyone know how much she made me work for her. She would even pay the dinner bill while I left the table just to let me know we weren’t on a ‘date’ … but in the end, I won!”

Carrying a bouquet that she created featuring white roses, baby’s breath, eucalyptus leaves and pampas grass, Chandler says her favourite moment was when she hilariously failed to repeat her vows.

“I got so lost in staring at Jake that I didn’t realize I was supposed to be repeating what Trevor said,” she says. “It was like in the movies, where things start moving in slow motion. That will forever be ingrained in my memory – staring into Jake’s eyes taking in what was happening, then realizing I was supposed to be talking!”

The couple then exchanged rings – Chandler’s a baguette cut diamond band.

Although her special day was tinged with sadness since her father Harry was unable to attend due to dementia and other health issues, Chandler honoured his English heritage with traditions like slipping a sixpence coin into her shoe. She also displayed a photo of her parents alongside her late mum Lucinda’s ashes, which were placed in an urn Jacob gifted her.

“It’s been really hard because my dad was so excited about the wedding,” she says. “Before he got dementia, he was constantly going, ‘Jacob, when’s the wedding?’ I’ve been struggling with that, but he would be proud that my brother walked me down the aisle.”

Following the ceremony, guests headed to a lavish 1600-square-foot suite at the Westgate Hotel, San Diego. But thanks to a room key getting stuck in the door, festivities were delayed 90 minutes before staff finally cut the lock so guests could pile in and enjoy a champagne tower and catering by local Italian restaurant Barbusa.

Chandler having changed into a show-stopping sparkly number by Russian label Albina Dyla, the fun continued at the Hard Rock Hotel San Diego rooftop bar, with late-night shenanigans involving Chandler and Trevor teaching Jacob how to skip as the trio frolicked down the street. The celebrations continued with New Year’s Day bar-hopping.

Having gone from O-Town’s end-of-year shows to Christmas then a New Year’s Eve wedding, by the time the newlyweds arrived at Mexico’s TRS Yucatan Hotel, they were ready for a spa day followed by the “best meal” of Jacob’s life.

“We were sitting on the Mexican Riviera with the ocean breeze in our face, drinking delicious wine, and eating steak, lobster, and octopus,” he says. “All the weight and stress of recent weeks lifted. We were finally just sitting across from each other – with no phones – going, ‘Wow.’”

Honeymoon fun also included visiting Mayan ruins in Tulum and the Playa del Carmen cenotes.

Now, as the couple look ahead to married life, they’re debating whether to expand their family, having “tried a lot last year.” In the meantime, they’re excited to spend 2022 travelling.

“With COVID, flying’s a pain, but we got a motorhome last year, so we’re going to live in the motorhome travelling around and visiting national parks in-between shows,” says Jacob, who has O-Town concerts coming up in California in February, followed by further “Pop 2000” tour gigs.

“Chandler grew up backpacking, hiking and always outdoors and we want to bring Evie up the same way. I’m looking forward to spending more time with my family on the road this year.”

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