Songfacts®:

• This heartfelt song comes from the wisdom of learning love lessons the hard way. We hear Garth Brooks cautioning a friend that "one day, you'll meet the girl you swore you'd never find." He continues:
  
  You'll push her away 'cause that's all you know how to do
  And then she'll leave and you won't beg her not to go
  Ask me how I know
  
  The song speaks to letting yourself love the object of your affections well, so you don't lose them.
• The song was written by country newcomer Mitch Rossell. He admitted to Taste of Country that it was based on personal experiences:
  
  "It came out straight from the soul and the heart of me always being that guy in relationships that had to have control and power, and wouldn't let anybody close enough to ever really love somebody," he said. "I pushed a couple of really good girls away because of that quality. It came from a very real place for me."
• Rossell first caught Brooks' attention when he'd pitched some songs for Brooks' 2014 comeback album, Man Against Machine. Though he didn't score any cuts on that record, the country star invited the newcomer to open some shows on his world tour with Trisha Yearwood.
  
  Some time later, Brooks was looking for songs for Gunslinger, so Rossell sent him "Ask Me How I Know" along with a few others. Not only did the country star choose to cut this tune, he also asked Rossell to play acoustic guitar on the recording session.
  
  "I just had to keep staring at the floor," Rossell recalled with a laugh of playing on the song. "When I looked up and saw all of those guys around me and knew all the records they'd played on, I was like, 'Oh gosh! Don't suck.' [Brooks] is standing there just belting this thing out, and I'm just cheesing the whole time, with this big, goofy smile on my face. It's almost like you're living something that's too big for you to comprehend."
• Brooks says that he and his team jokingly call Rossell "diva" because he never asks for anything.