In November, Chamberlain shared that she was "going through a breakup" during an episode of her podcast, two years after she was rumored to be dating McPoland.
While the 24-year-old internet star was interviewing celebrities on the Met Gala red carpet on May 4, her rumored former flame, musician Peter McPoland, sent the internet into a tizzy when he uploaded a cover of "Sally, When the Wine Runs Out," the hit song by another of Chamberlain's exes, Role Model (whose legal name is Tucker Pillsbury).
McPoland did not reference Chamberlain or Pillsbury by name, instead captioning his TikTok post, "Sally cover #fypシ #viral #awesome #nothingbutlove #foryoupage."
Fans quickly chimed in in the comments, with one writing, "There is layers to this video," while another added, "The amount of screen time it takes to understand the weight of this." One commenter suggested McPoland and Role Model collaborate writing, "Ok let's work it out on the remix!"
In November, Chamberlain shared that she was "going through a breakup" during an episode of her podcast, noting that the relationship had been "two years long." She had been rumored to be romantically linked with McPoland, 25, after the pair were spotted together at the 2024 Paris Olympics and wore coordinated Halloween costumes later that year.
Before McPoland, Chamberlain dated Pillsbury, 28, for three years before their split in October 2023.
When sharing the news of her latest breakup, Chamberlain said that she and her ex had "decided to remain friends."
"I've had quite a few boyfriends, but I've had very short breaks in between, meaning I haven't really been single. So it's a little bit daunting to be in this place now where I'm single again," she continued during the podcast episode. "This time, I know I should be single for a little bit longer than two or three months. I think this time I need to be single for like a year."
In December, as some fans speculated that a shadowy figure in one of her Instagram posts could be a new flame -- or perhaps even indications that she had rekindled with Pillsbury -- Chamberlain quickly shut down the rumors.
After one Instagram user commented, "did you get a new bf already 😭," the Chamberlain Coffee founder responded, "That is my DAD LOL."
Though she's been relatively quiet on her last two relationships, the content creator also made a rare reference to her romance with Pillsbury during a Nov. 28 appearance on bestie Owen Thiele's podcast In Your Dreams. During the episode, Thiele asked her, "Why do you keep dating musicians?," to which she responded with a laugh and borrowed another celebrity's words to explain.
"To quote Sabrina Carpenter, once again, 'I swear they choose me. I'm not choosing them,' " Chamberlain said. "And I choose them a little too."