Cheshire died Nov. 29 at the age of 46 and was the widowed husband of Luke’s only sister, Kelly, who died suddenly in 2007 when she was 39. The couple had three children, who are now teenagers.
Til – who joins Bryan’s two young sons, Bo and Tate, and wife Caroline at their home in Nashville – has two older sisters, who visit often.
“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, 38, told ABC News. “You just have to plow on and play the hand that’s dealt.”
The death of his sister left a particularly deep mark on the singer since it followed the loss of his only brother, who was killed in a car accident 11 years earlier at the age of 26.
“Losing my brother changed me tremendously and losing Kelly, even more,” Bryan told PEOPLE Country in 2013. “I literally do not take one second for granted.”