I make playlists based off the meaning or context of the song, as well as the character of the person I'm making it for.
So, for instance in your situation, I'd probably go with something like this:
1. Carlos Santana - Make Somebody Happy
https://www.youtube.com/watch?v=YRpaneW6WJE
2. Glenn Campbell - Gentle On My Mind
https://www.youtube.com/watch?v=NtiHluArFc4
3. Gypsy Kings - Love and Liberte
https://www.youtube.com/watch?v=DETw8JjCdxs
(more tunes go here... this is a short list... and then close it out with a bookender)
4. Carlos Santana - Angels All Around Us / Viva La Vida (Life is for Living)
https://www.youtube.com/watch?v=pgb8XB5PG0o
I left the tags off the vids so the thread isn't all jacked up with bandwidth.
*shrug*
YMMV