Disappointments
And as often happens with love, it’s unpredictable. Though it seems like the country star could have had any woman his heart desired, that wasn’t always the case. One of his love ballads was written about one of his first romantic rejections.

Kenny fell head over heels for a woman that didn’t reciprocate his love. There’s a bright side to everything, however, and this rejection birthed one of Chesney’s most successful songs. Naturally, many of his songs are based on his romances, and were inspired by women.