Tough Hearts Break Too: Jenna Paulette’s “How To Make A Cowboy Cry” is a Stunning, Soulful Tearjerker

Review By Emiko Taylor

Jenna Paulette returns with a tender, emotionally-charged new single that strips away the cowboy mythos and replaces it with raw vulnerability. “How To Make A Cowboy Cry” is more than just a beautiful ballad—it’s a lived-in love letter to life’s softest, most profound moments.

Written alongside Parker Welling and Casey Brown, and produced by Will Bundy, the track captures the emotional heartbeat of a man raised to be stoic, who finds himself moved to tears by life’s truest milestones. From wedding vows to the discovery of new life, it’s all wrapped in a melody as soft as prairie wind and lyrics that cut straight to the soul.

Paulette’s vocals are flawless—earthy yet angelic, confident yet gentle. She sings with the grace of someone who’s lived every word. Her performance paints vivid snapshots: naming a child before she exists, hearing Chris LeDoux while working cattle in Colorado, two pink lines that change everything. These are the moments that sneak past a cowboy’s steel exterior and go straight to the heart.

With her trademark blend of traditional country grit and modern emotional depth, Jenna Paulette once again proves why she’s one of Nashville’s brightest rising stars.

A quietly powerful track that proves even the toughest cowboys have a soft side. Jenna Paulette is writing from the heart—and it shows.