In case you’re feeling nosy and desperately need to know everything about Olivia Rodrigo’s love life due to being way too emotionally invested in her song lyrics, gather ’round! We are taking a respectful trip through her dating history—including, of course, the man who seemingly inspired the lyrics to “drop dead.” ​

It all started back in October 2023, when The Sun reported that Olivia traveled to London with her bestie, Conan Gray, to visit Louis and spend some time with him…and we’ve got the photos to prove it:

“They met through mutual pals earlier in the year and have been messaging quite a bit,” an insider for The Sun said at the time.

A beautiful, whirlwind romance followed, which included an official red carpet debut at the 2024 Venice Film Festival in Italy, a date night at the 2025 Grammys, a very loved-up Wimbledon appearance, and lots of PDA around NYC and London. They even sparked engagement rumors at one point…but by December 2025, The Sun reported that the two had gone their separate ways.

For what it’s worth: Neither has confirmed those split rumors, and fans are preeeetty convinced that Liv’s latest single, “drop dead,” was inspired by their romance.

Zack and Olivia started hanging out right around the 2022 Super Bowl—in fact, a source told E! News, “He invited her to Super Bowl parties that he was DJing that weekend and she went to support him. They hit it off and have been casually hanging out.”

Alas, these two ended up splitting just a few months later in August 2022, when a source told Us Weekly, “Their relationship sort of fizzled. They were casually dating but haven’t spent time together in a while. There were no issues—they both have different work schedules and different friend groups.”

Even so, the casual vibes didn’t stop fans from speculating that “Vampire” off of her second album GUTS was about Zack …though in a September 2023 interview with GQ, Zack went on the record about the song and said, “I don’t think it’s really about me. I think the internet just ran with it.”

He added that he “knows how a song gets made” and he didn’t think their relationship/subsequent split could warrant a breakup track: “We hung out, we’re both busy, and we ended up not furthering our relationship. There was never any drama, you know?”

Olivia and Adam were spotted together in the summer of 2021 while hanging at a Space Jam 2 event at Six Flags, as one does:

It's unclear when exactly they broke up, but a source wound up telling People in February 2022, “They’ve been over for a bit now.” There were also plenty of breakup rumors going around TikTok:

Side note: Some fans also think "Vampire" is about Adam, not Zack. The more you know!

Olivia and her High School Musical: The Musical: The Series costar Joshua Basset started dating on the show, and pretty much everyone thinks their breakup was the catalyst for Olivia writing this ol’ chestnut:

Joshua then wrote several songs about Olivia, including “Crisis,” which has not-at-all dramatic lyrics like, "Half the shit you’re saying’s only half true/Messing with my life as a career move/I can’t help but wonder why you won’t make it end?”

And he opened up about the speculation surrounding their split, telling GQ, “Why don’t we focus on these women for who they are? Let’s focus on the art that they’re making and how great they are instead of their relationship to a boy.”

Anyway, Olivia and Joshua seem to get along just fine these days. Here they are at the High School Musical: The Musical: The Series season 3 premiere back in July 2022!

Olivia and Ethan met on the Disney show Bizaardvark and had a short but sweet ’ship.

And it seems like they were/are still on good terms?

Anyway, that’s all, bye!