Songfacts®:

• Jamie Lynn Spears co-wrote this ballad with Connie Harrington and Tim Nichols. It was inspired by a conversation the trio were having about one of Spears' exes. "Connie was someone I had written with several times, and it's always nice writing with other females — especially when you're going through transitional kind of stuff," Spears recalled to Taste of Country. "Tim came in on one of the co-writes, and we were talking about how I was personally going through this time where the person I had been with, we were not together, but he was with another girl who was bringing out the kind of man that you want to see in the person you're with. And it was bittersweet for me, because I was like, 'You know, that's what I always wanted from him, but I'm almost at peace with knowing that he's gonna be okay.' She's bringing out the good in him, and that made me feel good."
  
  "It kind of snowballed off of that idea. It was a really clear point of view that everyone could connect to — man, woman, doesn't matter who you are, you've been there," she continued. "You've seen that person, the high school boyfriend or whoever it is, grow into the man that you never thought they could be."
  
  Once the threesome had the concept in pace, the song came about organically. "Connie was playing guitar, and me and Tim were talking over some ideas, and Connie started playing this melody, and with this idea it was really sweet," Spears recalled. "It just made perfect sense. It kind of all felt into place."
• As soon as Kramer heard the song, she readily identified with the lyrics, feeling that she had lived them firsthand. "It's a very true and honest song about my high school sweetheart Matthew. It's one of those that is as true as it can get," she told Billboard magazine.
• Kramer had been wanting to write a song about Matthew for years, but the words just wouldn't come. "(Producer) Scott Hendricks knew the story, and he called me into his office and said, 'You've got to listen to this song. I think you will relate to it.' I started bawling. That's the story," she said. "Those are the words that I couldn't write. It was 100 percent true."
• The sentimental video was directed by Kristin Barlowe (he shot Kramer's debut music clip, "Why Ya Wanna," as well). The visual was filmed in South Nashville, during an historic winter storm - which made the outdoor scenes a bit of a challenge. "We knew it was going to be cold, but we didn't know it was going to be that cold," Kramer told Rolling Stone Country. "I had the sniffles for about a week and a half... but it was so worth it."
• Kramer views the clip as a tribute to her high school sweetheart. "It was young love," she said. "I didn't want to tell 100 percent my own story because I wanted the listeners to interpret their own version. Every story is different. I even gave the video to my mom to watch, and she said, 'Wow, it brings me back to my days with Steve.' Everyone has that name [in their past]."
• When the song debuted at #92 on the Billboard Hot 100 dated October 31, 2015, it marked the first entry in any capacity on the chart for Britney's sister, co-writer Jamie Lynn Spears.