Cheshire was married to Luke's late sister Kelly, who died in 2007, and now, Bryan and his family are helping their three children cope with the devastating loss.
"We feel like if we just stay positive through this, maybe we'll be a positive inspiration for people that had these things happen to 'em," Bryan told ABC News. "You just have to plow on and play the hand that's dealt."
"It's every day on the phone all day trying to talk with the family and figure out what to do, but it's what you gotta do," he said. "Tough stuff."
Bryan admitted that he and Caroline are exhausted at the end of every day, but he tries to stay positive and tells himself that this is all part of God's plan.
"You know, we just stay positive. I think people expect that from me," he said. "I have to pray that people that have had similar situations can maybe look at my family and see me positively dealing with it. I'm not saying it's easy."
"That night we were, as a family, watching all of that on TV and watching Lady A and Stapleton sing that," he recalled. "It was a big-time healing moment."
Bryan's music career continues in high gear with the 2015 leg of his That's My Kind of Night tour launching next week. He'll release the new album, "Spring Break…Checkin' Out" on March 10.