Olivia Wilde Broke Protocol In A Big Way When Attending Colton Underwood's Wedding

"The Bachelor" Season 23 was memorable, to say the least. Here's the story: Former professional football player Colton Underwood started off the series with over two dozen women vying for his affection. The goal? Fall in love and get engaged. Over the span of two months (give or take), a slew of dramatic group dates, and several candlelit one-on-ones, the football player narrowed the group down to three contestants: Tayshia Adams (who went on to become Season 16's second Bachelorette), Hannah Godwin, and Cassie Randolph. 

After Randolph self-eliminated, Underwood entered full-on crisis mode and decided she was the one. In one of the most dramatic moments in the history of "The Bachelor," he sprinted and scaled a fence. Eventually, and with the help of some fool-proof TV magic, he won Randolph back and even introduced her to his parents. The pair began a real-world romance, but it was from a happily ever after.

In September 2020, Randolph filed for a restraining order against her ex, alleging that he stalked and harassed her in the months following their breakup, even installing a tracking device on her car. In November of that year, the charges were dropped. Underwood came out as gay in April 2021 — the Netflix documentary series "Coming Out Colton" followed his journey. Not long after he publicly came out, Underwood started dating Jordan C. Brown, and in May 2023, the couple tied the knot. Among their 200 guests was director and actor Olivia Wilde.

What's the number one rule of any wedding? Don't wear white unless you're the one getting married. At Colton Underwood's wedding to political strategist Jordan C. Brown, actor-director Olivia Wilde broke that rule. Wilde showed up in a silky white Nili Lotan gown and, along with the other wedding guests, carried a parasol. The "Booksmart" director joked about her taboo fashion choice in an Instagram story, writing, "Wore a wedding dress just so I could make a joke about it in my toast," and following it up with a bit of reassurance, explaining — "The grooms approved" (via E! News).

So, what's Wilde's connection to Bachelor Nation, exactly? She's had a long-time friendship with President Barack Obama's former campaign advisor and is even a regular guest star on his Instagram account. For reference, he's also posted pics with stars like Dianna Agron and Sophia Bush — Brown has no shortage of famous connections.

Even though both grooms supported Wilde's choice of dress, some fans weren't so impressed. "The internet is saying that Olivia Wilde is the definition of a pick-me girl," one TikTok user summarized. The director is no stranger to controversy, especially after the "Don't Worry Darling" drama. What's more, this comes shortly after her Met Gala dress was nearly identical to Vogue editor Margaret Zhang's.

"The Bachelor" wasn't on Jordan C. Brown's watchlist before meeting his husband. "I was so thankful and grateful that he didn't know what 'The Bachelor' was or who I was" Underwood shared with People. Although the football player-turned-reality star initially asked his partner not to watch the show, Brown eventually decided it was time to take the plunge, if only to satisfy curious fans. "I was like I gotta watch," he shared, remembering times when members of Bachelor Nation would ask him about the infamous fence-jumping moment.

The happy couple tied the knot in May 2023 ceremony in Napa Valley — along with Olivia Wilde, Chris Harrison (the franchise's former controversial host) and Bobby Berk of "Queer Eye" fame were also in attendance. "We wanted to approach this in a way breaking some of the traditional norms of what a ceremony and a wedding look like," Underwood shared with People, noting that many of their guests had never been to a queer wedding before.

Because he's always leaned towards long-term commitments, saying "yes" was a no-brainer for Underwood. When Brown proposed at Big Sur, the pair had been dating for just under a year — marriage felt like the logical next step. As for what the future holds? Another stint on reality TV might not be in the cards for Underwood, but he's excited to begin life with Brown and — one day — become a father. For now, however, they're happy parenting their two dogs.