Derek Jeter’s Dating Diamond Vs. 5 Other All-Star ‘Players’

Ryan Gosling, Ray J, Leonardo DiCaprio, Justin Timberlake and Brad Pitt challenge The Captain for the most famous dating history.

Last year “SportsNation” featured a graphic of Derek Jeter’s Dating Diamond. It was truly inspired, both the list and concept, which is why we remembered it again while watching Jeter’s impressive performance last night in his final All-Star Game.

This morning we began wondering if other celebrities have dating diamonds that can rival The Captain’s. Do they even have 10 notable names on their lists to fill a starting roster? We racked our brains. Did some crackpot research. And came up with five famous guys who have equally famous romantic histories: Leonardo DiCaprio, Brad Pitt, Justin Timberlake, Ray J and Ryan Gosling. Keep an eye out for a few girls who would have played on multiple teams.

What do you think? Whose All-Star lineup is the strongest? Who did we miss?

Ryan Gosling

Charlie Kasov

Justin Timberlake

Charlie Kasov

Ray J

Charlie Kasov

Brad Pitt

Charlie Kasov

Leonardo DiCaprio

Charlie Kasov

David Dean is the founder of Serial Optimist and writer of things that hopefully make you smile. Find him all over MTV, Thought Catalog, HelloGiggles and "Google."