Did Olivia O’Brien and Grayson Dolan Date? Here’s What She Said

It’s been a chaotic week for the Dolan twins. First, Emma Chamberlain’s podcast episode about a toxic ex—allegedly Ethan Dolan—blew up. And now,Olivia O’Brien might’ve just confirmed she dated Grayson Dolan around the same time. Oh, and her 2019 album Was It Even Real?? Yeah, fans think it’s all about him.

Keep reading for everything we know:

Did Olivia O’Brien and Grayson Dolan Date?

Neither Olivia nor Grayson ever confirmed their situationship, but the rumors point to them dating from 2018 to 2019.

Flash forward to January 2025, and Olivia subtly entered the chat with a TikTok that had everyone spiraling. She was seen mouthing lyrics from her song “Purpleworld” after Emma’s podcast went viral. The TikTok originally had the caption “lore mentioned” (👀), but Olivia later deleted the caption while leaving the video up.

The lyrics? “I’ve been talkin’ to your brother, he said that you found another girl. Hope she’s everything I wasn’t, I’m just from another world.” Fans are convinced the “brother” here is Ethan, making it clear the song could be about Grayson.

Was Olivia O’Brien’s Album ‘Was It Even Real?’ About Grayson Dolan?

Olivia once said the album was inspired by one person. Now, everyone’s betting that person was Grayson.

“I thought that this song [‘Purpleworld’] was a perfect intro to the album because it best describes how I felt about the person I wrote this album about and what happened between us. I held nothing back, writing this song was like a therapy session,” she told Paper Magazine in 2019, referring to the opening track of her album.

She also spilled major details about her messy love life back then, including how her ex was “still in love” with his ex-girlfriend at the time.

“I wrote this song [‘Care Less More’] about the same guy that most of the songs are about,” she explained in the same interview. “This guy was still in love with his ex-girlfriend the entire time we talked, and I knew that but somehow convinced myself I didn’t care. I always thought of myself as someone who was too independent for a relationship, but I liked this guy so much I would have set that rule aside for him. He wouldn’t have set it aside for me, so I told him (as well as myself) that I felt the same way just so I could keep him in my life. I thought that if I acted like I cared about him even less than he cared about me, he would like me more. The hardest part was that every time I thought there was no hope, he would say something sweet to me or give me an ounce of hope that he wanted to be more than what we were. No one’s ever complimented me the way he did, but his words mean nothing now that I know what his true intentions were. I learned the hard way that playing games never works out.”

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