This song is about a maintenance worker who is attracted to a high-maintenance woman in the complex he maintains. Keith told AOL Music about this song: "My manager T.K. met his ex-wife years ago when she was the head cheese at an apartment complex in Nashville. They had a basketball goal outside for the residents and T.K. would shoot baskets with the complex's maintenance man Curt while waiting for Betty to get off work. Curt eventually asked T.K. how he could get into the music business and, long story short, he's now one of the head guys at my booking agency Monterey Peninsula Artists. The three of us were at dinner one night and got to talking about Betty, who was just a country girl back at the apartment complex, but is kind of a high maintenance chick now. Likes her Dolce & Gabbana. T.K. said something about having known her for 20-some years, and Curt mentioned he'd known her a lot longer since they'd worked together before T.K. was in the picture. I asked Curt if he ever dated Betty and he said, 'No, she was too high maintenance for the maintenance man.'"

Though Keith wrote this song himself he gave co-writing credits to comedian and singer Tim Wilson and his co-writing partner Danny Simpson. He explained why on his website: "I got to the studio and played ('High Maintenance Woman') for the session guys and they said, 'Aw, man. There's a comedian named Tim Wilson who's got a skit about that and has a little ditty song that's kind of the same thing.'... Tim's a friend of mine, so I called him and told him about my song... I said I wouldn't even record mine without his blessing, which he gave. And just because I don't want anyone to ever think I copped his song, we threw him a small share of the writing and put (Tim and Danny's) names on it."

Keith performed this on The Colbert Report, where the host Stephen Colbert often pokes subversive fun at the conservative views and lack of subtlety in Keith's songs, notably "Courtesy Of The Red, White And Blue (The Angry American)" and the line, "We'll put a boot in your ass, it's the American way."

In 2014, Trace Adkins began performing a song with a similar theme called "Maintenance Man." Adkins song is more earnest with a blues feel, but shares similar hook: "High-maintenance woman, and I am her maintenance man." The song is included on his DVD Live Country!, released in January 2015.