Steven Tyler and Aimee Ann Preston (41 Years)
As the front man for one of the most renown rock bands in history, Aerosmith, 74-year-old Steven Tyler has been rocking arenas for decades while enjoying all the perks that one might expect of someone of his status, including dating beautiful, younger woman. In an effort to keep things consistent, Tyler hooked up with his very attractive, 35-year-old personal assistant, Aimee Ann Preston. They’ve been together as early as 2014 and appear to be going strong to this day.