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Time flies fast. Travis Kelce and Taylor Swift’s engagement photo is making the rounds on social media, drawing plenty of love from fans. Back in July, the Chiefs star shared a picture of himself and the Grammy-winning artist from a snowy Montana getaway with friends Erin Andrews and Charissa Thompson. In reality, the trip had taken place months earlier, in March.

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Thompson recently posted a few offseason pictures of her vacation, which quickly made Kelce nostalgic. The fifth slide had the picture from Thompson’s trip with Swift and Kelce. Longing for another trip with friends and loved ones, he wrote, “Football’s back!! But damn that offseason was fun!!” This was met with a playful yet motivating response from the FOX Sports reporter. “right! But we ALL crush the season , kick some a– & run it back next offseason,” he said.

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Well, the Chiefs’ tight end has already turned his focus back to football with just days left before the season opener. After falling short in Super Bowl LIX against the Eagles, the 35-year-old has been vocal about his desire to reclaim the team’s glory in his 13th NFL season. He wasn’t only vacationing during the offseason. “This year got some time to really focus on some form running and some things early on in the offseason that I just didn’t have time for last year. Certainly feeling good, and I think it will pay off,” he said.

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His underwhelming finish last year (four-catch, 39-yard performance in Super Bowl) only pushed him to sharpen his offseason training, shedding weight and focusing on mechanics. Patrick Mahomes backed him up, saying Kelce looks energized and ready to go. Though his current contract runs only through this season, Kelce’s sights are firmly on another championship. Off the field, he’s already scored a major win. He popped the question to Swift at his Leawood mansion. The two quickly shared the news with their family.

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Just days after she appeared on the Kelce Brothers’ podcast, both Kelce and Swift shared the picture on social media. “Your English teacher and your gym teacher are getting married,” the couple announced. And perhaps, this is just the perfect time to reminisce about their vacation in the Montana resort.

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Charissa Thompson recalled fondly vacationing with Taylor Swift

Erin’s husband, Jarret Stoll, and Thompson’s boyfriend, Steven Cundari, also joined the couple for the vacation. But it was found out only after Kelce shared the pictures on social media. Until then, the two broadcasters had stayed silent about the March trip. This week, on their Calm Down podcast, Andrews and Thompson finally opened up about what it was like spending time with the NFL star and the music superstar.

For Thompson, meeting Swift was nothing short of surreal. Both Andrews and Thompson had admired Swift for years, even before publicly nudging Kelce as a worthy match for her. Seeing that connection come full circle, Thompson felt it was rewarding. “I will say this. She is everything that I’d ever hoped and dreamed that she could have been, and more,” Thompson said.

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The broadcasters also explained why they kept the getaway under wraps. Both stressed that Kelce and Swift live under constant public scrutiny, and they felt it was important to let the couple control how their personal life was shared. “And they are so happy, and adorable and all things. So, when the opportunity came about for all of us to spend time together and go on vacation, we were elated,” she added.

When Kelce decided to post the photo without warning, Andrews jokingly commented, “So with that. Travis I’d really like some privacy. How dare you—I mean no photo approval on this end. What the hell my man?” However, she agreed that Kelce shared the best picture. “That’s one of my favorite photos from that trip we all took together. And yeah, I’ll echo it: she’s a 20 out of 20. She just is, she is so much fun. And I’ll just say this, our group, the six of us, we have some fun. Wow. A time. A good, good group.” 

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It clearly isn’t a bad idea to celebrate a little early.

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Pritha Debroy

3,476 Articles

Pritha Debroy works with the NFL Lifestyle Desk at EssentiallySports, where she explores the league beyond the sidelines and focuses on the cultural nuances of football. Bringing a fresh perspective shaped by her background in basketball lifestyle stories and cross-sport expertise, she highlights how NFL athletes build influence off the field. A graduate of the EssentiallySports Journalistic Excellence Program, our in-house initiative that trains writers under industry experts, Pritha specializes in long-form features and player-driven stories that capture the evolving identity of today’s NFL stars. Pritha combines her passion for storytelling with a thoughtful approach to sports culture and lifestyle. With strong communication skills and an eye for detail, she brings a distinctive voice to NFL journalism, delivering engaging and insightful content that resonates with readers.

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Ridhiman Das

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