Zach Bryan‘s littlest fan has now gotten to meet the star not once, but twice.

While out on his current the Quittin’ Time Tour, Bryan has made a habit of walking out through the crowd to greet fans as he heads to the stage. Last month, during a stop at the Boston-area Gillette Stadium, one of the fans he met during his walk-out was a five-month-old baby boy named Leo.

Leo’s parents handed him over to Bryan, and the country superstar posed for a photo op, looking equal parts excited and terrified to be holding the infant. The adorable fan moment made the rounds on social media, with many chiming in to say that they were jealous of baby Leo, who’d gotten to meet one of country music’s biggest stars before he could even walk and talk.

The baby’s parents were excited, too: Dad Logan D’Agostino posted the video on his Instagram along with the comment, “Can’t wait to show our son this when he’s older!!!”

But that wasn’t the end of little Leo’s hangout sessions with Bryan. Less than a month later, the singer returned to Gillette Stadium for another show — and yep, Leo and his parents were in the crowd. Once again, they held the baby out front and center as Bryan came towards the stage for his walkout, and once again, the singer stopped to say hi.

“Again?!” you can see Bryan mouthing as he spots Leo in the crowd. He’d started strumming his guitar as he walked up towards the stage, but when he saw the baby, he halted the music and once again reached out to pose with Leo for photos.

On Instagram, Leo’s parents shared some more photos and videos from the special night, with the infant smiling in his headphones before the show and snoozing on his mom’s chest later on during the night.

Bryan’s Quittin Time Tour is scheduled to continue into mid-December.

Carena Liptak is an Associate Editor and staff writer at Taste of Country. She specializes in breaking country music news, interviews and lists. In particular, she’s got a soft spot for sad songs — check out her roundup of the 50 Saddest Country Songs of All Time!