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."
Samantha, for her part, laughed off the curiosity surrounding their relationship in 2008. "Even the airport security guy in Canada asked me, 'So is it true?'" she told Harper's Bazaar at the time. "It's like, 'Oh, yeah, I'm telling you.'"
When They Peaked: The time Lindsay twinned with Samantha and borrowed one of her signature fedora hats at the airport.
The Breakup: Though their relationship was often on-again and off-again, LiLo and Sam didn't officially go their separate ways until April 2009.
The breakup was messy. According to a source at People, Samantha "changed the locks on her house" and "banned" Lindsay from attending an event celebrating her sister Charlotte Ronson's fashion brand immediately following the breakup. "Sam's family has made her swear that it's really over," a friend of Lohan and Ronson's previously told the outlet. "They are giving her all the support they can to keep her away from Lindsay."
Lindsay was reportedly blindsided by the split, which she said, "came out of nowhere." During an appearance on The Ellen DeGeneres Show, Lindsay revealed, "I had no idea what was going on. I just hadn't seen her in, like, a week. She, like, disappeared." Lohan wouldn't confirm exactly what led up to the breakup but assured fans that infidelity wasn't the reason.
Reflecting on their separation months later, Lindsay admitted that Samantha is the only woman she'd ever consider being with again. "I never really thought about women before; it kind of just happened with Samantha. It surprised me," she told The Sun. "If I weren't with Samantha, I would probably be with a boy next. She's the only woman I've been attracted to."
Where They Are Now: Since splitting from Samantha, Lindsay was linked to NFL alum Matt Nordgren, Russian businessman Egor Tarabasov, and the crown prince of Saudi Arabia, Mohammad bin Salman. Lohan is now married to financier Bader Shammas. The two, who both live in Dubai, were engaged for seven months and dated for three years before tying the knot in July 2022.
Lindsay majorly scaled back her acting career and took a break from the spotlight after moving to Dubai in 2014. However, she will next be seen opposite Chord Overstreet in Netflix's Falling for Christmas, later this year.
Ronson is currently in a relationship with beauty guru Cassandra Grey of Violet Grey. The two have been dating since 2017 and live together in Los Angeles.
Professionally, Samantha is still spinning records, and one of her most recent DJ'ing gigs was at The Veuve Clicquot Polo Classic in Los Angeles last year. She was also featured on the 2021 single "Freedom Train" by Toots & The Maytals.