The 67-year-old singer and Preston, 28, stepped out together at Elton John AIDS Foundation's Oscar Viewing Party late last month, reported Ace Showbiz.
Preston and Tyler and have appeared together in public with him numerous times in the past but never in an intimate way.
Preston reportedly has been Tyler's assistant since 2014. In that same year, the pair were spotted holidaying in Maui, enjoying the sunbath and kayaking.
Tyler has a history of dating much younger women.
Before that, he was married to former Andy Warhol model Cyrinda Foxe and clothing designer Teresa Barrick.
Two of his four children, Liv Tyler and Mia Tyler, are older than Preston.
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