Van Morrison is a great choice but don't use one of the expected tunes (Brown Eye Girl or Moondance), but rather go for his rendition of "Someone like you". A classic tune that is beautifully sung.
A youtube link to check it out:
http://www.youtube.com/watch?v=vVpgIm37RKw
Great selection for the dating part.
For one of her growing up Leanne Womack's "I Hope You Dance" is real nice but someone expected.