Songfacts®:

• This is about Kristi Hansen, a friend of Kenny's who passed away in 2012 from a brain aneurysm at the age of 35. The singer first met Kristi in the US Virgin Islands in the 1990s and she was part of a group of pals whom he would hang out with during his downtime in the Caribbean. He recorded this touching tribute to her as the closing track of his sixteenth studio album, Life On A Rock. "This record was tough for me in the studio, especially that one," the Nashville star told Billboard magazine. "To sing a song that personal - about someone who really touched your life was hard for me. It really was. There's a difference in singing something like ' Pirate Flag,' 'When The Sun Goes Down,' or ' Summertime' in the studio, and getting in there and singing a song like that. This record was so emotional and so close to me."
• The Hey Now was a boat that Chesney would hang out with in the Caribbean with his friends and he considered Kristy the centerpiece of all of them. Chesney explained to Billboard magazine: "This person defined that circle of friends, she defined a time in my life when it was a lot simpler for me. I think that she was the kind of person that lived the kind of life I really craved. She was the epitome of living life in the moment. She took life like it was a big lemon and squeezed it really hard. I think we all have somebody in our life that dies young, and it's hard to figure out why, and that can make such an impact that no matter how busy you are and what you're doing in life, it can stop you in your life and change you. That's what it did to me, even before I wrote this song. When that happens to you and you have to let go of someone you really care about, it makes you re-evaluate everything. It makes you re-evaluate the connection with the person you're in a relationship with, what you're giving to it, are you giving to it. It makes you re-evaluate your relationships with your family, your friends, and that's what Kristi's passing did to me. It changed me as a person, as an artist and songwriter, the way I like to walk through the word. She was a special person."
  
  "Some people are really good at math, good at school," he added, "some have a great business mind, some are great at sports. Kristi was good at life and that's what this song is all about."