kenny chesney is a great country sinfger dated a sexy brunette named stephanie but broke up with her tragicly, is engaged to whitney delora wynn but is cheating with his ex...hint hint.
Term used to describe men on online dating sites who only post pictures of themselves wearing a hat, sunglasses, or both to hide the fact that they are unattractive, cross-eyed or bald.
"This guy's cute but I totally think he has Kenny Chesney Syndrome, he has a hat on in every picture"