In 2004, Jay-Z released his instant classic “99 Problems,” which details the many problems in his life, expect romantic love. Fast forward over 20 years, G’Ra Asim is facing his own set of problems, except they all focus on modern romance.

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Contemplating his singledom and mishaps in dating, Asim takes us through a thoughtful meditation on chronic lovelessness. Using a process he calls “thinkful wishing” as an antidote, 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.

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99 Problems Finding the 1 offers cultural critique, contemplation, and experience from a millennial in search of a partner. For example, Asim observes how 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.

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His bold dissection of modernity serves a central claim: admittedly a problematic fave, love is worthy and capable of reclamation and redemption. Even as white supremacy gets in the way, Asim argues that we’ll have to abandon the posture of terminal cool and hazard a little earnestness to bring love back.