One of my favorite longing for a love song is "Black Haired Boy' written by Grey DeLisle. Here are the lyrics:

Black Haired Boy
Oh, where's the little black haired boy with shining eyes of blue
Where's the little black haired boy that bid my heart adieu
I wandered in the valley and swam across the sea
I prayed the good Lord's mercy would bring him back to me
Oh where's the little black haired boy with shining eyes of blue
Come home now little black haired boy, my heart belongs to you

Be joyful little black haired girl, your boy's not been untrue
Be joyful little black haired girl for since we bid adieu
I toiled in the valley and drowned beneath the sea
I prayed the good Lord's mercy redeem and rescue me
Be joyful little black haired girl, your boy's not been untrue
For though my spirit's heaven bound my heart belongs to you

    If you Google Grey DeLisle and "Black Haired Boy" you can hear her singing this beautiful song.


For Category 2, I would put my vote in for John Prine's "In Spite of Ourselves". Again, if you Google the song you can probably find the lyrics.