“I Hope You Don’t Mind Me Writing,” the closing track of Jessie Dipper’s 2025 EP I’m a Mess, is a devastatingly beautiful exercise in musical letter writing. Released in December 2025, the song functions as a raw, unfiltered update to a lost friend, arriving with a seasonal poignancy that cuts through the typical holiday noise. It is, quite simply, one of the most courageous pieces of songwriting released this year.
The track’s power lies in its specificity. Dipper navigates the “seventeen long years” of absence by grounding her grief in the mundane and the momentous: she mentions her move to Wales, her marriage, and the surreal experience of watching siblings grow older than the person who left. By framing the lyrics as a literal letter, Dipper avoids the abstract metaphors often found in songs about loss, opting instead for an intimacy that makes the listener feel like they are over-hearing a private, sacred conversation.
Musically, the arrangement is masterfully sparse. Recorded with a live, organic feel, the track features Dipper’s signature acoustic guitar work accompanied by the sensitive piano playing of Chris Holley. This minimalism allows Dipper’s vocal performance to take center stage, her voice carries a weight of “nostalgic ache” that never tips into melodrama, maintaining a conversational tone that underscores the song’s sincerity.
The accompanying music video, directed by Luke Furmage and released on December 19, 2025, uses virtual production to create a dreamlike space that mirrors the song’s themes of memory and distance. For anyone who has carried a “silent conversation” with someone no longer here, “I Hope You Don’t Mind Me Writing” provides a much needed vocabulary for the long term journey of grief. It is a haunting, healing conclusion to Dipper’s discography.
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