Reba was quite taken with the song, but she had reservations about singing it because she had just gone through a divorce from her longtime husband Charlie Battles. Reba thought that listeners might interpret her performing the song as a reflection that she had regrets about the divorce, which she absolutely did not. This was a decision that she had thought long and hard about, and determined it to be the right thing to do. There was no turning back.
In the end, Reba decided to record “I Know How He Feels,” not because it was the way she felt about her divorce, but because she deemed it a great song, and knew beyond a shadow of a doubt that it was a hit.
Reba’s recording of “I Know How He Feels” featured an unusual production technique. There were no drums whatsoever through the first verse and first chorus, although the arrangement grew as the record progressed. “I Know How He Feels” debuted in Billboard at #59 on September 10, 1988 and reached number one a dozen weeks later (pretty much an average ascension time) on December 3rd, marking Reba’s eleventh of her 25 Billboard chart-toppers. She is tied with Dolly Parton for the most number one hits by a female country artist.