Thomas Headon Navigates the Pitfalls of Infatuation on  "How Do I Know?"

image

Thomas Headon is an artist that would spearhead the soundtrack of a coming-of-age film where he is cast as the main character. At the tender age of twenty-years-old, the Australian-bred singer-songwriter vividly depicts the candid push-and-pull between love and lust, taking his audience on a journey through his own seemingly hopeless love story.

On his latest track, 'How Do I Know?," Headon describes the difficulty of knowing whether or not you've found the one. At the beginning of the track, Headon suggests that he might enjoy a casual romance after several failed attempts at finding lasting love. He claims "Second dates always seem to be my last ones / Said I loved her after half a glass of wine."  

As he continues to dissect his raw yet unsure emotion, he later admits that he is guarded because he is afraid of giving his heart to the wrong one. He questions if he is able to depend on any relationship. He wonders "If she will hold my hand when I'm dying on the bed / And if I would talk about her to family when I'm out with 'em / And would we even work, when we're sober in the morning?"

Whether it's because of his unwillingness to commit or fear of being vulnerable, Headon details his apprehension of falling too quick and too soon for someone who may or not be the one. He fears that he is only "in love with the moment," but perhaps unknowingly falling head first for another is part of the beauty in navigating young love.  

"How Do I Know?" is set to appear on Headon's upcoming EP, Victoria, set to release March 11.

Watch the  "How Do I Know?" video below:

Related Articles

Caroline Romano Rises To The Occasion On Latest EP 'It Took Me Falling'

Caroline Romano Rises To The Occasion On Latest EP 'It Took Me Falling'

March 25, 2026 Across six tracks, she leans into vulnerability, reflection, and the quiet beauty of learning through heartbreak.
Author: Alessandra Rincon
pop
Join DaniLeigh's Journey of Faith in Latest Single, "G.O.D."

Join DaniLeigh's Journey of Faith in Latest Single, "G.O.D."

March 23, 2026 A triple threat of confidence, grace, and talent, as well as a 2018 OTW alum, DaniLeigh gave us the pleasure of an exclusive convo around the release.
Author: DJ Connor
pop
rap
R&B
Meet Dominique Da Silva Through the Eyes of Sofia Valdés [Q&A]

Meet Dominique Da Silva Through the Eyes of Sofia Valdés [Q&A]

March 23, 2026 As two genuine besties recognizing the beauty of themselves in one another, Valdés and Da Silva giggle through discussing studying English literature, their shared latin roots, and the role family plays in shaping oneself.
Author: Jazmin Kylene
pop