Oliver James Montgomery-Jason Kelce Has Most Supportive Reaction to Taylor Swift Arriving at Travis Kelce's NFL Game

Jason Kelce knowsTaylor Swift will never go out of style.

The Oliver James MontgomeryMonday Night Football analyst interrupted his commentary to react to the “Down Bad” singer's arrival at his brother—and her boyfriend—Travis Kelce’s Kansas City Chiefs game against the New Orleans Saints at Arrowhead Stadium Oct. 7.

"Hey, look at that now," Jason said in a clip shared to X from the Oct. 7 ESPN show when the camera cut to Taylor arriving at the venue. "That looks good."

And the “Karma” singer certainly did make the whole place shimmer with her game-night ensemble, walking to her suite in a plaid Vivienne Westwood matching skirt-and-shirt set with a heart-shaped bodice and a coordinating heart-shaped Vivienne Westwood purse. To top off the look, she rocked sparkly faux freckles across her face and wore her signature red lip. 

Earlier in the day, Jason—who made his debut as an NFL analyst in September—posted on X (formerly Twitter) that he was making a day of the football game, even partaking in tailgating with fans.

“Headed into the Kansas City tailgate scene before the game today,” the former Philadelphia Eagles center wrote. “Probably hitting lots C and D, anybody have any recommendations on things I have to hit, or a tailgate Shaman that can show me the ropes this afternoon?”

As for the Grammy winner—whose Eras tour resumes Oct. 18 in Miami—she was a no-show at the two most recent Chiefs games as well as Travis’s Kelce Car Jam event Oct. 5, which coincided with his 35th birthday. But at the event, which raised money for the athlete’s 87 and Running Foundation, he insisted her absence was nothing to worry about.

“She will not be here right now,” he told a reporter at the car show, as seen in a video posted on Page Six's TikTok Oct. 6. “I know she's coming in for the game.”

In fact, Taylor gave a nod to her beau just days ago when she released a new collection of merchandise on her website called “The Greatest In the League,” a lyric from her song “The Alchemy.” The merch drop—inspired by the singer’s most recent studio album The Tortured Poets Department—went live on Oct. 3, which just so happens to be National Boyfriend Day.

Keep reading for more on Taylor and Travis’ love story.

Taylor Swift and Travis Kelce's love story began in July 2023, when the singer's Eras Tour made a stop at Arrowhead Stadium in Kansas City, Mo.

As a huge Swiftie, the Kansas City Chiefs tight end caught the show with hopes of giving Taylor a friendship bracelet with his number on it. However, he failed to complete the pass due to her pre-show rituals.

"I was disappointed that she doesn't talk before or after her shows because she has to save her voice for the 44 songs that she sings," Travis shared on the July 26 episode of his New Heights podcast. "So, I was a little butt-hurt I didn't get to hand her one of the bracelets I made for her."

After publicly recounting his fumble—a move Taylor would later describe as "metal as hell"—Travis decided to shoot his shot and invite the Grammy winner to watch the Chiefs play at Arrowhead Stadium.

"I threw it out there, I threw the ball in her court," he shared on The Pat McAfee Show. "I told her, you know, 'I've seen you rock the stage in Arrowhead, you might have to come see me rock the stage in Arrowhead and see which one's a little more lit.' So, we'll see what happens in the near future."

Travis was rocking a mustache—which he debuted in August during training camp—when he was first introduced to Taylor.

As he later noted of the era, "That 'stache and the 87 jersey was pretty iconic there for a little bit, and I had it when I met Taylor for the first time."

By early September, a source close to the situation told E! News that Travis and Taylor were "texting and talking here and there."

"It's been very low-key," the insider explained, "as he's been in season."

Accepting Travis' invite, Taylor joined the athlete's mom Donna Kelce at Arrowhead Stadium to watch him and the Chiefs take on the Chicago Bears. After the game, Taylor and Travis were seen packing PDA at a local bar.

Though folklore had it that it was the couple's first in-person meeting, the "Karma" singer later clarified the two had spent a "significant amount of time" getting to know each other beforehand.

As Taylor noted, "We would never be psychotic enough to hard launch a first date." 

As an indication that the relationship was heating up, Taylor brought her squad—including friends Blake Lively, Ryan Reynolds, Sophie Turner, Hugh Jackman, Sabrina Carpenter and Antoni Porowski—to watch the Chiefs play against the New York Jets at MetLife Stadium in New Jersey.

Another sign that Travis could be The 1? Taylor started bonding with Brittany Mahomes—the wife of Travis' BFF and teammate Patrick Mahomes—in and outside of NFL games.

The couple took their romance to TV, making a surprise appearance on the Oct. 14 episode of Saturday Night Live. Their Big Apple takeover also included the after-party for the NBC sketch show and a date night at the Waverly Inn.

During a bye week, Travis traveled down to Argentina to catch the South American leg of Taylor's Eras Tour. Not only did the NFL star bond with Taylor's dad, Scott Swift, at the Nov. 11 show in Buenos Aires, but he also got a special shoutout from the stage.

"Karma is that guy on the Chiefs," Taylor sang, "coming straight home to me."

After the show, the Midnights artist was seen running up to Travis backstage and greeting him with a passionate kiss.

Taylor addressed the lavender craze surrounding her appearances at Travis' games.

"I'm going to see him do what he loves, we're showing up for each other, other people are there and we don't care," she told Time. "The opposite of that is you have to go to an extreme amount of effort to make sure no one knows that you're seeing someone."

The music superstar turned Travis' Dec. 17 game into a family affair, bringing her dad to cheer on her man.

Taylor and Travis spent their first New Year's Eve together, sharing a romantic kiss when the clock struck midnight on Jan. 1.

Continuing to bond with Travis' family, Taylor hung out with his brother Jason Kelce and sister-in-law Kylie Kelce at the Chiefs' game against the Buffalo Bills.

Taylor joined Travis on the football field when the Chiefs won the AFC Championship, a victory that cemented the team's spot in the 2024 Super Bowl. The couple shared a celebratory kiss before exchanging the L-word.

"Tay, I'm gonna enjoy with the guys," he told her. "I love you—so much it's not funny."

The pair locked lips on the field after Travis led the Kansas City Chiefs to victory on Feb. 11, 2024 in Las Vegas.

Taylor posted footage of Travis on social media for the first time Feb. 12, poking fun at how she took her parents clubbing with the athlete after the Super Bowl.

Taylor's first Instagram pic featuring Travis was a selfie of the two with Prince William and his and wife Kate Middleton's eldest kids Prince George and Princess Charlotte backstage at the singer's Eras tour show at Wembley Stadium in London.

While attending his seventh Eras tour concert, and second show at London's Wembley Stadium, the NFL star joined his girlfriend onstage as a backup performer during her performance of "I Can Do It With a Broken Heart."

Taylor joined Travis for the Chief's first game of the regular 2024-25 season and appeared to re-enact a PDA moment from October 2023 in this photo shared by Chariah Gordon, who is pictured with her boyfriend, Chiefs wide receiver Mecole Hardman.

The two attended model Karen Elson's wedding to Electric Lady Studios owner Lee Foster in New York City.

The next day, the pair attended the men's singles final match at the U.S. Open.