Created by Nuyorican street kids in the mid-1980s, freestyle music became the sound and the story of second-generation Boricuas. Hip-hop and pop, Latin Caribbean rhythms and instruments, it all came together in freestyle. The sound was ubiquitous in New York — and later in Orlando, Florida, where many of these second-gen Borinqueñse were charting new ground and new lives across the diaspora. 

Artists who were young Puerto Rican women ultimately became the face of the genre; and for the listeners that so resembled them, the music provided an opportunity to dance to the beat of someone who looked and sounded like them. Young freestyle artists sang about love, heartbreak, and their sexual desires. In Lisa Lisa & Cult Jam’s “I Wonder If I Take You Home”  — one of the genre’s biggest hits — a young woman sings about her sexual desire, on her own terms and without shame. 

As a Boricua born in the ’90s, reporter Raquel Reichard didn’t experience the freestyle explosion in real time, but she’s felt its profound ripple effects. In this episode, we meet two mother-daughter duos – including Raquel and her mother – for whom “I Wonder if I Take You Home” is particularly special. The song opened intergenerational conversations around sexuality, respectability and empowerment. And while impacting their lives both personally and professionally, it also strengthened their relationships with each other.

Illustration by Mya Pagán.