As any other young person back in 2018, I was an avid watcher of Emma Chamberlain’s YouTube channel.
As said avid watcher, I was invested in Chamberlain’s Spotify account, as she would make aesthetically pleasing playlists with indie music she enjoyed. In 2020, Chamberlain added a song called “blind” by Role Model to her playlist, unbeknownst to many that the song was most likely written about her.
This song marked the beginning of a blossoming relationship with singer-songwriter Role Model, aka Tucker Pillsbury. That relationship lasted three years, coming to an unfortunate ending in September 2023.
And yet, here I am, still not over it. Probably won’t ever get over it—ever.
They belong together, and here’s why.
Relationship Origins Recap
Pillsbury discovered Chamberlain in March 2020 via TikTok when her account came across his For You Page (FYP). The TikTok showed Chamberlain dancing to a Dayglow song. He reached out to her via direct messages, and the two connected from there.
Pillsbury, in July of that year, released a song called “blind,” which he allegedly wrote for Chamberlain, describing how he was mesmerized by her. Chamberlain later added this song to her Spotify playlist, while rumors about their relationship remained unconfirmed.
After years of subtly hinting at their relationship with cryptic Instagram posts, Hollywood parties, Halloween costumes, and random paparazzi moments, the pair officially “hard-launched” their relationship on Valentine’s Day 2023 for a GQ interview.
The relationship lasted three years, coming to an unfortunate ending sometime in September 2023 or October 2023, hence the lyric, “Am I thinking ‘bout September” in Pillsbury’s song, “Some Protector.”
As someone who was a fan of both, in their own right, I was devastated to hear about the breakup.
As with all celebrity breakups, it's confusing as to why it happened, although Pillsbury later hinted at events that led to their breakup in interviews prior to his sophomore album and lyrics weaved throughout “Kansas Anymore,” released in July 2024.
“I was going home a lot and kind of again creating space and leaving LA a lot and not really having a reason why to tell that person,” Pillsbury said in a May 2024 interview with Zach Sang, giving a reason for his breakup with Chamberlain.
“I just wanted to go home alone and be with my friends and family and like have some normalcy and I think that would be very confusing for the other person. I think it’s like ‘Why are you running away from me?’” Pillsbury added.
Although there were some answers as to what led to the breakup, whether in interviews or song lyrics, it didn’t seem like a malicious ending. It was the long distance that separated the couple, leading to a feeling of disconnection which ultimately ended the pair.
Recent Events
In late November, Chamberlain went on Owen Thiele’s podcast, “In Your Dreams,” where she discussed being newly single.
For context: Following Pillsbury and Chamberlain’s breakup in 2023, Chamberlain went on to date another singer-songwriter named Peter McPoland, whom she dated for two years. Last month, Chamberlain announced their breakup on her own podcast, “Anything Goes.”
On Thiele’s podcast, Chamberlain and Thiele joked about how Chamberlain dates musicians who write songs about her.
“To quote Sabrina Carpenter, ‘I swear they choose me, I’m not choosing them, amen,” she laughed.
When talking about how she met her now ex, McPoland, Chamberlain said she didn’t know he was a musician until after meeting him.
“I thought ‘Oh no, we’re doing this again,’” Chamberlain said.
“Aw sh–t here we go again,” Theile sang after, referencing Chamberlain’s ex Pillsbury, and his song, “Sally When the Wine Runs Out.”
“Enough,” Chamberlain said. “Leave that in.”
Like many Pillsbury and Chamberlain fans, this made me think, “What does that mean?” making me hope there’s something going on between the two behind the scenes.
But that’s not all that happened. Thiele posted a reel to promote the podcast episode with Chamberlain, where she danced to Pillsbury’s song, “Sally When the Wine Runs Out.”
As a fan of Pillsbury’s music and someone still not over Chamberlain’s breakup with Pillsbury, I was shocked to say the least, as Chamberlain stayed relatively quiet about Pillsbury following their breakup. It’s like Chamberlain wanted Pillsbury to see her dancing to his music, to capture his attention and possibly rekindle something old.
Pillsbury hasn’t responded or commented on any of Chamberlain’s recent actions, however, fans joked about Pillsbury’s reaction to Chamberlain’s reel. They also joked about how nobody should show it to him, given his lyrics and album.
Chamberlain, however, did say she needs time to be single for a while on her podcast episode, “embracing being single.” She noted that she tends to wait 2-3 months between relationships, stating that she now needs time to be single in her life.
“I think this time I need to be single for a year,” Chamberlain said.
Why They Belong Together
There are multiple reasons why I feel the pair belong together. First being that in 2022, Pillsbury revealed that Chamberlain was his first-ever girlfriend.
He told GQ he was closed off to the idea of a relationship prior to Chamberlain, fearing the impact it would have on his music. By allowing himself to open his heart to Chamberlain, it is clear that she is a special person to him.
As of this year, Pillsbury appears to be single since his split from Chamberlain, which makes me believe that Chamberlain was someone special to him. He’s either taking his time to move on and heal, or feels he can’t quite exactly replace Chamberlain. Either way, she clearly has meant a lot to him, which is why they belong back together.
To many, especially myself, it also appears that Chamberlain is Pillsbury’s lyrical muse. This is another reason why they belong together.
Prior to Kansas Anymore’s debut, Pillsbury released his song, “Oh Gemini,” as a single, which would later be featured on his album. The song hinted toward his feelings toward Chamberlain—a common theme echoed throughout his album.
“But, without you, what am I? Oh, Gemini/Please remember my name,” Pillsbury sings.
Obviously, Chamberlain’s astrological sign is a Gemini, so Pillsbury is clearly singing about her in his song, expressing his regrets and lamenting the relationship.
Also, on Pillsbury’s album, the song “Frances” succeeds “Oh Gemini.” Frances is Chamberlain’s middle name.
“Frances/She was amazing/She held my hand in times like this,” Pillsbury sings.
Again, Pillsbury references his relationship with Chamberlain in his music, describing how Chamberlain was toward him and where he felt he messed up. He is apologetic, while reflecting on times the couple shared and the hardship he caused the relationship.
Pillsbury is clearly inspired by her, and it is clear, through many of his songs, that he thinks fondly of her. With Chamberlain’s recent comments and actions indirectly directed towards Pillsbury, it’s clear this couple should get back together.
It’s obvious something is still there between the two of them. Their time apart only allowed them to grow, but now it’s time for them to get back together.
So where’s your Sally, Tucker? I know, and she’s closer than you think.
Dominique Mercadante is the Editor-in-Chief of The Setonian. She can be reached at dominique.mercadante@student.shu.edu.
