’90s Flashback: Jennifer Love Hewitt’s “How Do I Deal” Still Holds Up

In this franchise, we look back on our favorite bops — both hits and underrated gems — from the 1990s.

Most people remember Jennifer Love Hewitt as the star of TV shows like Party Of Five and Ghost Whisperer, or for her iconic role in I Know What You Did Last Summer, but she also dabbled in pop for much of the ’90s. After dropping three albums with little success, the singer/actress finally struck gold with “How Do I Deal” in 1999. An angsty teen-pop anthem with a sing-along chorus, the song reached number 59 on the Billboard Hot 100 after being featured in I Still Know What You Did Last Summer (i.e. the sequel).

Bizarrely, “How Do I Deal” captures the monotony of Quarantine Life in modern-day America with eerie accuracy. “Every day I wake up to another day gone by,” JLH chirps at the beginning of the song. “Nothing but the open road and a never ending why.” I remembered this as an upbeat bop — at least by ’90s standards — but it just gets bleaker from there. “Every night in the dark, I lie awake in bed,” Jennifer laments. “How am I supposed to dream with all the static in my head?” I too would like the answer to this question.

That takes us to the chorus. “How do I deal with you? How do I deal with me?” the one-time teen idol ponders, plunging ever deeper into an existential crisis over jaunty guitars. “When I don’t even know myself or what it is you want from me.” I always loved this song and still take great pleasure from Jennifer’s BareNaked, particularly the title track and “Can I Go Now.” (Fun fact — both songs were co-written by Meredith Brooks of “Bitch” fame). The multi-hyphenate has released a couple of random songs since then, but I live in eternal hope of another album. Revisit “How Do I Deal” below.

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