When I think about Brad Pitt and tropical New Year celebrations, my gossip mind immediately goes to January 7, 2005 – a big day in gossip history. That’s when he and Jennifer Aniston announced that they were separating after ringing in the new year in Anguilla. You remember this photo, don’t you? This photo was taken exactly 16 years ago today, January 5, 2005. 

Brad Pitt and Jennifer Aniston on vacation in the Caribbean, January 5, 2005
Brad Pitt and Jennifer Aniston on vacation in the Caribbean, January 5, 2005

That’s partly why it was so confusing to people at the time. They seemed to be so loving in that moment – after years of being Hollywood’s dream power couple, here they were, kissing on the beach, and how could it all have been not a reassurance of their union but in the end, a goodbye? At the time, when the paps were photographing them, no one had any idea that two days later, on a Friday, they would make a joint announcement that they were ending their marriage. These were the pictures that branded themselves on our gossip memories when that statement came out– that they “remained committed and caring friends”. It was supposed to be amicable then. Until, well, you know. 

It’s now 2021. And it was another tropical New Year’s celebration for Brad – only this time in Turks and Caicos, and he’s not with an ex or a current love, but with Flea, shot a couple of days ago while snorkeling. Brad is now single after whatever it was that you want to call it with model Nicole Poturalski this past summer which his sources have clarified was NOT a relationship. Per PEOPLE:


"Brad hasn't seen Nicole since August. It was never a relationship," the source said in October. "They saw each other a few times and that's it. You can't call it a split, because they were never together in the first place. It was a casual fling and that's it." 

LOL at the fact that he found himself in a situation with a much younger woman who is still married to another much older man where it was preferable to characterise it as a “casual fling” instead of… a proper romance? A convenient, um, arrangement? I mean, yeah, that’s how weird the optics were on that, ahem, experience. 

Anyway, Brad was reportedly supposed to spend part of the holidays with three of his children – Shiloh, Knox, and Vivienne – although, as we know, it has been years since he’s been seen in public with them. Or maybe it would be more accurate to say …since they’ve been in public with him?