This is the second single released by America Country music group Gloriana from their sophomore album A Thousand Miles Left Behind. It was also the first song to be heard from the band after they became a three-piece, following the departure of Cheyenne Kimball. The song was made available for purchase on October 4, 2011.
Band member Tom Gossin told Billboard magazine the story of the song: "It's a song I co-wrote with Josh Kear," he said. "We got together, and started talking about life. Two hours later, we had a song. It's a song about a guy and a girl on the first date. It was kind of inspired by my experiences on first dates, because I was always really shy, and had a hard time making that move for the first kiss. So, in this song, the guy chickens out at the end of the date. Then, he gets back out of his truck, and the girl is hoping for the same thing. Then, they reconvene back on the porch."
Gossin and Kear also drew inspiration for the song from a chance encounter Tom had at a restaurant earlier in the week. "Coincidentally a couple days before this I had overheard a conversation a group of girls were having," he explained to The Boot. "I was eating, and they were at the next table. One of them had been on a date with a guy, and she was like, 'Did he kiss you?' She was like, 'No, he didn't do it at the end. It was a great date and he didn't do it at the end, and I don't know why.'"
Gossin discussed the song with Billboard magazine. He said: "A lot of the songs on the album talk about the person we would all like to be. You can have your alter ego come in and do all the things you can't really do in real life, like not making the first move at the end of a date, but wishing you had. This is a song about the attempt to never end up with regrets. That's another theme on the album - the worst thing is to look back on something and be like, 'I wish I had done things differently.'"