Songfacts®:

• On "Single Again" Josh Ross invites an old flame to reconnect if she ever finds herself single. The song gently wrestles with the bittersweet notion of timing in relationships, that space between what was, what might have been, and what still could be.
• Ross wrote "Single Again" alongside Joe Fox (Joe Pardi's "Last Night Lonely," Dylan Marlowe's "Boys Back Home") and Brad Rempel. If Rempel's name rings a bell, it might be because he's one-half of Canadian country duo High Valley, the guys behind "Make You Mine" and "She's With Me."
• The song was birthed one night at Losers Bar in Midtown Nashville, where Ross ran into a girl he'd had a crush on all through high school. "I hadn't seen her in like eight years," he recalled to Billboard. "I brought her a drink, walked up, and found out she had a boyfriend. It was just casual conversation, but maybe it was the couple of drinks I'd had. I told her, 'Hey, let me know if you're ever single again.'"
  
  The line stuck with him. Ross typed it into his phone, adding a note beneath it: "The one that got away."
  
  For nearly three years, it sat there, a forgotten scrap of inspiration. When it finally resurfaced in a writing session, Joe Fox helped shape the hook while Brad Rempel pushed for the big, anthemic chorus and melody that brought the song to life.
• Matt Geroux produced the song. A Nashville-based music producer, songwriter, engineer, and mixer, Geroux has helmed most of Ross's notable tracks, including his first Gold-certified single, "Trouble."
• Released on January 12, 2024, "Single Again" was the second single from Ross's EP Complicated and a bona fide chart climber. It topped the Mediabase Canada Country chart and marked Ross's first Top 10 on Billboard's Country Airplay chart.