Who: Teen Choice Award-winning actress and singer Lindsay Lohan, 36, and DJ, singer, and songwriter Samantha Ronson, 45.

How They Met: The beginnings of Lindsay and Samantha’s relationship aren’t entirely known, but if we had to guess, the two probably met at a Hollywood club — I mean, where else did two incredibly hot and famous humans meet in the early aughts?

After a few years of platonic friendship, things took a romantic turn in 2008 — and before long, Lindsay and Sam were spotted everywhere together: sitting front row at Ronson’s sister’s fashion show, at parties posted up in the deejay booth, and on double dates with their moms.

Lindsay never directly confirmed she and Samantha were a couple but alluded to the relationship on her MySpace blog. And in November 2008, she told Harper’s Bazaar, “I think it’s pretty obvious who I’m seeing. I think it’s no shock to anyone that it’s been going on for quite some time… She’s a wonderful person, and I love her very much.”

Why We Loved Them: They were one of the first queer “It Couples” in Hollywood. Lindsay and Samantha got together during a time when it was still rare to see a same-sex relationship in Hollywood, but they never apologized for it.

“I was bold enough to say, ‘Yeah, I like a girl. And?'” Lindsay recalled back in 2012, adding that Samantha was “attacked every day” by the media over their romance. She echoed a similar sentiment a few years later, telling E! News that she often felt judged for dating Samantha. “Samantha Ronson was my best friend,” Lohan said. “At that point, I actually was kind of the first young person straight off the Disney train, so it was a big deal. My younger siblings didn’t know what to make of it.”