Songfacts®:

• This lighthearted Chris Gelbuda and Jeff Silbar penned song finds Currington playing sidekick as his friend gets the girl. He told Billboard magazine that it's a scenario he can identify with. "I think everybody has been in those shoes at least once in their life," said the singer. "You have a wingman, you go out, and you expect him to back you up. But, sometimes it doesn't happen. He ends up stealing the girl at the end of the night. I've seen that happen before. I think I've been a part of that before. When I heard that song, it made me laugh, and I thought that others might find it funny. Surely, I'm not the only one that's been there."
• Currington's own "Wingman" is a friend he's had since his high school days. He explained: "I still have a guy named Jamie Day, my best friend in the whole wide world, and he's my wingman, always will be."
  
  Currington added that on hearing the demo for the single "Hey Girl" for the first time, he was flooded with memories of Jamie and him chatting up girls. "'Hey Girl' is what we used to say while we were walking down the beach when we didn't know what else to say," Currington explained, "and Jamie was always that wingman for me. If either one of us couldn't come up with something, that was the one line we would use, and it would always start conversation. Every time."
  
  "I've known Jamie since the fifth grade," Currington concluded "He ended up sitting in front of me, and we just became the two class clowns and got in a lot of trouble together, and it just kept going from there."