After billionaire pop queen Taylor Swift announced her grand engagement to game show host Travis Kelce, a former flame entered the chat.
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“Your English teacher and your gym teacher are getting married,” the “So High School” singer captioned a dreamy post about her engagement to Happy Gilmore 2 star Kelce earlier this week.
It’s only fitting that Swift and Kelce used high school imagery in their big announcement… because a man claiming to be the Cats star’s flame back in high school has stepped forth… and thrown down something of a gauntlet.
Taylor’s self-proclaimed high school ex, Andy Slye, proudly resurfaced on X with a throwback photo of the two, likely from 2008. In the snapshot, teenage Andy is beaming from ear to ear like he just won the lottery, while Swift offers a polite, borderline “blink twice if you need help” smile. They don’t exactly scream young love, but hey, props to Slye for swinging for the stars.
“That feeling when your girlfriend from high school finally gets engaged,” Slye wrote alongside the awkward snapshot. “I used to tell myself: Andrew, it’ll be okay. She wasn’t right for you. I just hope her husband isn’t some handsome buff football player.”
That feeling when your girlfriend from high school finally gets engaged.
— Andy Slye (@slye) August 28, 2025
I used to tell myself: Andrew, it’ll be ok. She wasn’t right for you.
I just hope her husband isn’t some handsome buff football player. pic.twitter.com/DEAmy45QHc
Of course, Kelce isn’t just a pro football player… he’s the only jock beau 35-year-old Swift had dated after an exhaustive laundry list of artistic types (even John Mayer!!!).
Taylor Swift’s Self-Proclaimed High School Ex Seemingly Makes Her an Offer in Wake of Her Engagement
In follow-up tweets, Slye opened up about what he’s been up to since taking an awkward snapshot with… er, I mean, dating Taylor Swift.
“I wouldn’t have hit it off with my wife if it weren’t for Taylor. Taylor was a topic the first time we met. We bonded over the music,” he explained.
He then dropped a not-so-subtle hint about what he’s angling at…
“Now we film weddings as a husband-and-wife team. We love to film football weddings (like this ND one). Is anyone else thinking what I’m thinking?” he added.
Meanwhile, plenty of X users took Slye’s bait.
“Looks like you’re a wedding photographer… Maybe she can use one coming up?” one onlooker speculated. “She might have a limited budget. We’ll see,” Slye jokingly shot back.
“Which song of hers was about you?” another X user asked.
“The one where she says, ‘I love the gap between your teeth,’” Slye quipped.
Could the stars align for Andy Slye and his wife to film Taylor Swift’s fairytale wedding? Only time will tell…