Trying to build rapport with a girl.

Sent her a christmas message a few days ago, the standard funny text you send to your entire phone book. She replied something like "Thank you, bla bla bla, I don't care much about christmas anymore". I took the cue and asked her why. She said it's because it's only she and her mother, so it's always a depressing time of year. I said I can relate to that because I also come from a small family, etc.

Tomorrow, should I send something like "Marry Christmas *girl name*. You may have a small family but you do have people who care about you."

Would that be seen as a sweet move and allow me to take advantage of the situation, or would it be a wuss nice guy move?

Or would you play it entirely different?