Some spoof! At tour's end, "All on Me" singer surprised the headliner on stage with his favorite drink

Products in this story are independently selected and featured editorially. If you make a purchase using these links we may earn commission.

When it comes to being the victim of end-of-tour pranks, Brett Eldredge is one lucky guy. After all, his perpetrator, opener Devin Dawson, has had a few naughty tricks up his sleeve.

Consider his ping-pong ball caper: Veteran prankster Michael Ray was the target of that one last year when Dawson and his band meticulously wrote the phone numbers of Ray’s band and crew, along with the initials “MR,” on 500 ping-pong balls and poured them onto the audience from a balcony.

“They were getting phone calls and FaceTimes and everything for weeks and weeks and weeks,” Dawson says with a satisfied smile.

Brett Eldredge and Devin Dawson
| Credit: John Shearer/Getty

This time around, for the last show of Eldredge’s recent The Long Way tour, Dawson tells PEOPLE he cooked up a surprise that had his headliner just laughing: As Eldredge made his entrance for the New York show, he found Dawson and his band members mimicking the lyrics of opening song, “The Reason,” by smoking cigars and sipping drinks at an on-stage bar. Dawson reached out and handed the surprised star an old fashioned, his favorite drink.

The 29-year-old Dawson and his band actually hung out on stage for a few songs because, as he says, “I was gonna finish my drink.”

Eldredge didn’t seem to mind — plus he got to take home more cigars, whiskey and custom-etched highball glasses. Dawson knows he went easy on his target, but then why irritate the guy you’ve just signed on to tour with in the fall?

“We might have to up the ante a little bit at the end of the fall tour,” Dawson warns. “We’ll see what happens.”

Considering the success — and fun — of Eldredge’s first major headlining tour, it’s no wonder the “All on Me” singer re-enlisted for another leg.

The vibe was easygoing, Dawson says, with “no boundaries” between artists, band and crew. “It’s cool to know that everyone’s friends,” he adds.

Among the highlights for Dawson were pickup basketball games with the 6-foot-5 Eldredge. Standing almost a head shorter, Dawson was no fool: He always made sure he was on Team Brett. (Not that Dawson is a slacker. “I can steal and I can pass,” he says. “I’ll hit a three every once in a while.”)

Devin Dawson

Life on the tour, Dawson says, didn’t offer much downtime between radio station visits, meet-and-greets, and the shows. But he always made time for a morning workout and regular phone calls and video chats with his girlfriend, singer-songwriter Leah Sykes. She also was able to accompany him to April’s ACM Awards show, the first time they walked a red carpet together. (She’s since joined him at the CMT Music Awards, as well.)

Says Dawson, who was an ACM new male artist nominee: “It was cool to have her there by my side and have her supporting me.”

Devin Dawson and Leah Sykes
| Credit: John Shearer/Getty

But by mid-evening, the tables were turned a bit as Dawson found himself on what he calls “shoe duty,” toting Sykes’ uncomfortable high heels.

Standing during a commercial break, he’d forgotten he had them in hand when he felt someone staring at him. “I look and it’s just Nicole Kidman sitting right there and she’s laughing,” Dawson recalls, “and I’m like, ‘What’s so funny?’ And she says, ‘I just think it’s hilarious that you’re carrying her shoes. I think it’s the cutest thing in the world.’ … So the first time I met Nicole Kidman I had my girl’s high heels in my hand. … That’s ‘All on Me’ in real life right there: When you need me to hold your shoes for you, I got you.”

Devin Dawson
| Credit: John Shearer/Getty

For his latest single, “Asking for a Friend,” Dawson has moved from feel-good romance to a more complex story song. What seems to start out as a pickup line turns out to be a plea for a second chance. The lyrics were inspired, he says, by a need “to say sorry to someone,” but he also was drawn to the opportunity for some clever wordplay with the catchphrase.

“I loved the double entendre of saying, ‘Hey, I’m just asking for somebody else,’ and it’s really for yourself,” he says, “but then, also, like, ‘I need a friend right now … I miss you. I’m sorry for what I did.'”

RELATED VIDEO: Snake in Toilet Interrupts Brett Eldredge’s Tropical Vacation

And no, Dawson says, he would never resort to that sort of coy pickup line. “I’m a very cut-and-dried kind of pickup-line guy: ‘Hey, I think you’re gorgeous. I would love to take you to dinner sometime.'”

Devin Dawson and Leah Sykes
| Credit: Jeff Kravitz/FilmMagic

That’s exactly what worked on Sykes, he says, after the two became acquainted through several chance encounters. Together for almost a year and a half, they enjoy being mutually supportive of each other’s music, Dawson says: “I think it works because there’s just confidence and respect from both sides.”

Continuing to promote his debut album, Dark Horse, Dawson heads out later this month as the opener on multiple dates for Tim McGraw and Faith Hill‘s Soul2Soul tour.