Lyric discussion by newdisaster 

Cover art for Dear Boy lyrics by Paul McCartney

I don't think this song had anything to do with John Lennon, despite his paranoia. I think it's just an example of Paul's absolute finesse of the ballad.

To me, this song fits well with a situation I went through in my life (tangent: I'm a girl, so I usually ignore the chorus with "her love" and all that, and focus more on me telling this to a "dear boy"). You love someone, they love you, but they throw you away for somebody else even though you two were perfect together.

Especially the lines "And even when you fall in love, dear boy, It won't be half as good as this" remind me of that snarking hurt of being replaced, or of being led on and let down. I feel that Paul is saying something along the lines of "You had it all, this love was perfect, but you didn't see it or didn't want it ("looked to hard", "never do become aware", "never knew what you had found") and now you've lost/missed it/your chance at it and i don't care how bad you want it back ("i hope you never know how much you missed").

Just my two cents.