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99 Problems Finding the 1

a love story (sort of)

Part cultural criticism, part picaresque adventure, professor and punk musician G’Ra Asim tackles chronic lovelessness in the post-covid era with heft and humor

In 2004, Jay-Z released “99 Problems” and song became an instant classic. The Grammy Award-winning rapper details the many problems in his life, expect romantic love. Fast forward over 20 years, professor and punk musician G’Ra Asim is facing his own set of problems, except they all focus on modern romance.

Contemplating his singledom and mishaps in dating, Asim takes the reader through a literary, speculative, and thoughtful meditation on chronic lovelessness. Using a process he calls “thinkful wishing,” Asim scopes out modern love, romance, and ambivalence to manifest a more loving and lovable future. Or at least someone he can list as his emergency contact.

Drawing on literature, history, sports, music, science and more to untangle the riddles of human connection, 99 Problems Finding the 1 offers critique, contemplation, and experience as a millennial in search of a partner. Scenes from his life as an early-career Black academic in an overwhelmingly white university environment display the challenge of finding someone to dote on in his dotage. Asim observes that ascendant Black folks rarely reach “cruising altitude”—a professional plateau stable enough to focus one’s overtaxed attention on vetting potential partners. On tour with his band, he ponders the relationship between stage banter and the seedy underbelly of social awkwardness. Along the way, he dishes arresting and acute takes on everything from 90s hip hop posse cuts to French absurdist theater to the Boltzmann Brain hypothesis. Each chapter invites readers into “discussions for another day.” The book’s bold dissection of modernity serves a central claim: love, admittedly a problematic fave, is nonetheless worthy and capable of reclamation and redemption.

Reflecting on his own capacity to love, Asim argues that we’ll have to abandon the posture of terminal cool and hazard a little earnestness. 99 Problems Finding the 1 is one heart’s dreamwork unfurled as a blueprint, for shaping our intimate and broad interpersonal future.