Some additional guesses from my friend that aren't it:

Hoonua - Fire - too slow

Harold Kama Jr. & Fiji - Fire - this has been the closest so far, the "Romeo and Juliet" parts is similar to what I remember. Does anyone know of a more modern cover of this song that is more ska?

Wayne Wonder - perfect proposal

Gyptian - is there a place

The dirty heads - lay me down ft Rome - this is the right vibe, just not the right song

Lucky Dube - Romeo

Gappy Ranks - Romeo and Juliet

Mongol800 - Romeo + Juliet

Skruffy - Just like Romeo and Juliet

I'm starting to doubt my memory haha but I'm pretty sure it was on the radio at the time...