Texas-born, LA-based writer and strategist Helen Donahue has worked with Playboy, Vice, and cult underwear brand Thinx among others, making creative copy an art form while excavating issues at the intersection of mental health and pop culture, like why we really need to rethink the vilification of Monica Lewinsky. You also might know her from her painfully funny, enviably minimalist Twitter handle @helen.

This Valentine’s Day, Document asked Donahue to soundtrack our perennial, bittersweet, increasingly annoying desire for people who don’t love us back. Her playlist includes Leonard Cohen, indie darling Chairlift, and T-Swift’s iconic anthem for the bespeckled and lovesick. If you never sat with your iPod Shuffle on the bathroom floor, weep-singing ‘she wears high heels, I wear t-shirts,’ you’re a stronger person than I am.