Models Galore
The tech tycoon and the top model - it's a tale as old as time (or, we guess, as old as the dot com boom). When it comes to Jack's Little Black Book, at least, there's apparently no shortage of swimsuit models to choose from.
In the past, the Twitter founder was linked to Sports Illustrated star Raven Lyn Corneil (whom he reportedly purchased an L.A. pad for in 2019) but he's more recently been spotted frolicking on Miami's South Beach with bikini babe Flora Carter.
[Photo via @flora_carter]