After divorcing from actress Talia Balsam back in 1993, Clooney's adopted a very strict "no marriage" policy, and his string of flings over the course of the last two decades has done nothing to suggest his stance will change.
From co-stars to models to waitresses to WWE wrestlers to Oscar winners, Clooney's dating history is one for the ages.
And now there's no denying that they've rekindled their love. But let's look back at what went down before this mushy makeup.
Brooks, who's part of the Aussie boy band The Janoskians, tweeted Saturday after Grande's set: "I am so proud of you and you looked gorgeous, well done on your amazing performance how do u dance so well wearing heels? After a string of tweets, she replied: “noooo you’re the cutest. Legend has it the young couple met on Twitter, when Jai and his twin brother Luke had some sort of crazy Twitter campaign to see who could score a date with the Nickelodeon star. The songstress' camp insisted that Brooks had actually broken up with her over the phone long before anything turned romantic with Sykes — no cheating scandal here! Just two weeks before Brooks' Twitter essay, Grande and Sykes, who had a new duet together, confirmed they were an item.
TMZ reports the former co-stars and maybe couple dined together in L. In fact, they haven't even talked publicly about their relationship.
Gyllenhaal is all about getting drinks with his girlfriends — we're pretty sure he and Taylor Swift's short-lived romance was solely based on their shared love of maple lattes.
But the real proof came in the last week, when their PDA and Twitter gushiness started back up.
You can tell a lot about a person from the people they date, and the one main thing you can tell from Cameron Diaz's dating resume is that she doesn't have a type.
There's another star in the Jake Gyllenhaal Ex-Girlfriends Club.
The actor was dating super hot model Alyssa Miller, but turns out the actor rang in 2014 as a single man.