Howard was put on blast by a 16-year-old who claimed to be his sidechick.
The girl posted screenshots of his text messages and tweeted a photo of him with her in a hotel room.
He has since denied the rumor, but most accept it as true anyway.
This is one of the smallest age differences on this list and we certainly can't fault Jeff Garcia for marrying a 25-year-old when he was 37-years-old himself.
The former Canadian Football League (CFL) quarterback finally broke into the National Football League as a member of the San Francisco 49ers in 1999 and went on to have a very productive ten-year career, despite getting a late start.
You likely wouldn't bat an eye if we told you Wayne Gretzky divorced Janet for a stunning 25-year-old blonde, despite the fact Wayne would be 26 years her senior.
Nor would you be shocked to learn that Joe Namath is chasing after a 30-year-old - he did, after all, profess he wanted to kiss ESPN's Suzy Kolber in an unflattering moment on air in 2003.She made no mention of any sexual acts between the two, but noted Dwight referred to her as his princess and that he broke her heart.