Taylor Swift’s High School Ex Has Hilarious Reaction To Her Engagement

Taylor Swift’s high school ex, the same Drew immortalized in her 2006 breakout hit “Teardrops on My Guitar," is finally breaking his silence on her headline-making engagement to Kansas City Chiefs star Travis Kelce. Swifties have long wondered how Drew, the boy behind one of her earliest heartbreak anthems, felt about being etched into pop culture forever. Now, nearly two decades later, he’s laughing along with fans as Taylor Swift trades teenage heartache for a real-life fairytale ending.

Taylor Swift's Famous Ex Breaks Silence On Her Engagement

That feeling when your girlfriend from high school finally gets engaged.

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

— Andy Slye (@slye) August 28, 2025

In a tongue-in-cheek post, Drew quipped about watching his teenage girlfriend finally find forever love. “That feeling when your girlfriend from high school finally gets engaged,” he wrote. “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.”

The self-aware jab immediately caught attention, given Kelce’s status as one of the NFL’s biggest stars, and arguably the definition of a “handsome buff football player.”

Drew Credits Swift For His Own Love Story

TEARDROPS ON MY GUITAR COMPLETELY HEALED ME #NashvilleTSTheErasTour pic.twitter.com/Kh80UGLs5I

— yising (@yisingkao) May 6, 2023

Drew didn’t stop at one post. He followed up with another, tying his life full circle back to Swift and the world of football. In it, he shared how his own marriage and career as a wedding filmmaker with his wife started with a bond over Taylor’s music.

“I wouldn’t have hit it off with my wife if it weren’t for Taylor,” he explained, noting they first connected by talking about her songs. Now, the couple films weddings together, often at football stadiums, and he hinted at a dream gig with the line, “We love to film football weddings… Is anyone else thinking what I’m thinking?”

The Legacy Of 'Teardrops On My Guitar'

18 years ago today, Taylor Swift released ‘Teardrops On My Guitar.’ pic.twitter.com/IwFoxikmpo

— Pop Base (@PopBase) February 19, 2025

Released on February 19, 2007, as the second single from Swift’s self-titled debut album, “Teardrops on My Guitar” quickly became the song that defined her early career. Inspired by her real-life high school crush, Drew Hardwick, the ballad captured the raw emotion of unrequited love and gave fans their first taste of Swift’s confessional songwriting style.

The track climbed to No. 13 on the Billboard Hot 100 and became a crossover success on both pop and country charts, helping cement Swift as one of music’s most promising new voices. It went on to earn multi-platinum certification from the RIAA, selling millions of copies worldwide, and was nominated for multiple awards, including a CMT Music Award.

More than just a hit, “Teardrops on My Guitar” became a cultural touchstone for fans, introducing the world to Swift’s gift for turning teenage heartbreak into timeless anthems. And with Drew’s name forever etched into the lyrics, the song continues to be one of the most iconic entries in Swift’s discography.

Taylor Swift And Travis Kelce’s Fairytale Engagement

As The Blast reported, Swift and Kansas City Chiefs tight end Kelce are officially engaged, marking one of the most talked-about celebrity love stories of the decade. The couple, both 35, began dating in the summer of 2023 after Kelce famously admitted he failed to give Swift a friendship bracelet at her "Eras Tour" stop in Kansas City. What started as playful banter quickly blossomed into a full-fledged romance that captivated fans and dominated headlines.

Over the past two years, Swift has been a fixture at NFL games, often spotted cheering in the stands alongside Kelce’s family, while he returned the favor by supporting her on the road during her record-breaking tour. Their love story came to a milestone moment when Kelce proposed earlier this week, with reports describing the engagement as intimate yet grand.

The Boy Behind ‘Teardrops’ Tips His Hat To Taylor’s Fairytale Ending

18 years ago today, Taylor Swift released Teardrops on My Guitar.pic.twitter.com/kXv17SqBqn

— About Music (@AboutMusicYT) February 19, 2025

In the end, Drew might have been the boy who left Swift in tears on her guitar strings, but he’s clearly in on the joke now.

Nearly twenty years later, he’s happily married, running a wedding business, and cheering on his high school ex as she prepares to say “I do” to an NFL superstar. Talk about a full-circle moment, even Swift would agree, that’s a lyric-worthy ending.