As Valentine’s weekend arrives, Questlove follows his love-inspired soundtrack with a different kind of selection, one pulled from the side of the crate reserved for heartbreak. He suggests ten songs that sit with loss, loneliness, and love that’s run its course, spanning Jazz and Soul laments from Donald Byrd and Les McCann to more modern reflections by Mayer Hawthorne and Cleo Sol.

Along the way, he shares the stories, anecdotes, and personal reflections that make these records ideal companions for a good cry — and, maybe, a little clarity.

If this year finds you on the hurting or healing end of love, consider this episode your solace.

See omnystudio.com/listener for privacy information.