What she had been working toward was documented in the album that she eventually released in 2014, under a set of circumstances that were entirely different from the major-label pop trajectory. Heartstrings was released on October 28, 2014, through Vagrant Records and her own imprint, Hotly Wanting. All nine tracks were written by Meester. The album was produced by Jeff Trott, who had worked with Sheryl Crow. The genres it drew on — folk, dream pop, alternative rock, indie pop — were significantly different from the pop singles that had preceded it.
The album’s tracks include “Heartstrings,” “Run Away,” “Good for One Thing,” “Sweet,” “On My Side,” “L.A.,” “Dreaming,” “Blue Afternoon,” and “Entitled.” Total running time is approximately thirty-one minutes. Critics received it with what most reviews characterized as positive, if modest, notices. It was not a commercial event in the way that “Good Girls Go Bad” had been a commercial event. It was a document of a musician with a specific sensibility making the music she was actually interested in making, with her own money and on her own creative terms.
She has been clear about why this mattered to her. “I’m not necessarily trying to make a living off music or get into the Top 40,” she told Vice. “Singing is my second career.” The music was not a bid for pop stardom; it was the expression of something she had always done and was going to continue doing regardless of whether the commercial math worked in its favor. She recorded some of the album’s material in Budapest while Gossip Girl was still in production. The song “L.A.” drew on the experience of having built a life in Los Angeles, a city she had moved to as a teenager and that she had come to know with the specific intimacy of a long relationship.