Jackson Olson’s Missed Chance with Taylor Swift: A Baseball Player’s Regret

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Jackson Olson
Jackson Olson's Humorous Take on Unrequited Love (Credits: CT Insider)

Jackson Olson is a Professional Baseball player and a TikTok star who is primarily based in America. Jackson Olson has been an inspiration for millions with his quality content on TikTok and creative ideas. Jackson was born on October 6, 1997, in New Milford, CT, America.

Jackson attended his school at New Milford HS and completed his graduation from Stetson and Hartford University. Jackson is the son of Laura and Dan Olson. Jackson highly participated in sports like Basketball, football, and baseball during his High School period but gradually increased his interest in baseball. 

Jackson is very active on Instagram and is a huge fan based on Instagram for his stylish videos and pictures. He is considered one of the personalities on Instagram, which is always trending with his videos. Jackson usually makes lip-sings Tik, TikTok videos, and comedy videos.

Jackson is very influenced by Modelling and regularly posts pictures on the Instagram account. Jackson started his Professional Baseball career in the year 2017 and appeared in 38 games.

Jackson Olson
A Playful Dig at Celebrity Crushes: Jackson Olson vs. Taylor Swift (Credits: New Milford Spectrum)

Jackson Olson’s Humorous Take on Unrequited Love

Jackson Olson, a Savannah Bananas exhibition baseball team member, humorously acknowledges the unlikelihood of becoming Taylor Swift’s beau due to recent rumors linking the pop icon to NFL star Travis Kelce.

In a TikTok video posted on September 13, the 25-year-old Olson performs a lip sync rendition of “The 1,” a sad ballad from Taylor Swift’s 2020 album Folklore, which explores themes of lost love. His fellow teammates provide him with emotional support as he conveys his sentiment onscreen: “When you had no chance with Taylor Swift but see she’s dating Travis Kelce.”

Jackson Olson
Jackson Olson’s Humorous Take on Unrequited Love (Credits: Boston Herald)

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A Playful Dig at Celebrity Crushes: Jackson Olson vs. Taylor Swift

To emphasize his decision to move forward, Olson captions the video with, “It’s officially time to move on,” and on his Instagram, he humorously tags himself as “Mr. Americana & The Heartbreak Princess.” This lighthearted clip quickly gained traction, amassing over 4.7 million views on TikTok and eliciting numerous comments on Instagram.

The Social Media Storm: Jackson Olson’s Viral Response to Taylor Swift’s Love Life

While neither Taylor Swift nor Travis Kelce, both 33 years of age, have addressed the dating rumors publicly, Kelce did reveal that he attempted to connect with the singer during her Eras Tour stop in Kansas City in July.

Jackson Olson
Jackson Olson’s Missed Chance with Taylor Swift: A Baseball Player’s Regret (Credits: Polish News)

Expressing his disappointment that Swift does not engage in pre- or post-show conversations to preserve her vocal cords for her extensive setlist, Kelce mentioned on 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.”

Kelce further explained to his brother and co-host, Jason Kelce, how Swift’s fans often exchange friendship bracelets. He mentioned receiving several of these bracelets but expressed his desire to give Taylor Swift one with his contact information.

Jackson Olson’s TikTok Take on Taylor Swift and Travis Kelce

In light of these developments, fans have been speculating whether Taylor Swift, who ended her six-year relationship with Joe Alwyn in April and briefly dated The 1975 rocker Matty Healy, might reciprocate Travis Kelce’s interest.


Even Jason Kelce acknowledged being aware of the rumors surrounding his brother and the Grammy-winning artist, humorously noting, “Everyone’s been infatuated with Travis’ love life.” During a September 14 appearance on TNF Nightcap, he added, “I don’t really know what’s going on there… I know Trav is having fun; we’ll see what happens with whoever he ends up with.”

As for Jackson Olson, his fandom for Taylor Swift is evident, from sporting merchandise from her 1989 era to persuading his teammates to listen to her music. He even attended one of her concerts during the summer, capturing himself singing along to “Lover” and “New Romantics” from the audience. In a video captioned, “When you’re in your lover era at the T Swift concert, but you haven’t found your wife yet,” Olson playfully acknowledges his Swiftie phase.

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About The Author

  • Sahil Salunkhe

    Hey, I'm Sahil from Mumbai. Here I'm to write about Movies, TV Shows, and News about new things. You can reach out to me at sahilsalunkhe.02@gmail.com

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