I was listening Magic 105.4 earlier. They played Papa Don’t Preach by Madonna. The girl in the song pleads with her Dad to let her see someone he disapproves of.
Next in the playlist was Uptown Girl by Billy Joel. A young man laments that the woman he has fallen for is from a different social class.
It occurs to me that these two songs are Pop Pairs. They could be two views on the same relationship.
My sense is that you could probably make a Pop Pair out of any two songs where the singer declares their love for someone else. But the really great pop pairs will be two songs that present two sides of a less conventional relationship. For example, Young Girl by Gary Puckett, paired with Born Too Late by the Poni-Tails; or Money Money Money by ABBA, paired with Gold Digger by Kanye West.
Alternatively, where the sentiment is quite specific: The particular question asked by the Shirelles in Will You Still Love Me Tomorrow is answered quite specifically by the Waterboys in How Long Will I Love You?