We normally do Angel Tree or similar gift opportunities at the holidays, but this year I'm aware of a family I know just a bit that is facing some real financial hardship. I'm thinking of getting a nice gift card from the local supermarket (which includes a gas station and pharmacy) and another from Target, and just sending them anonymously in a Christmas card from "Santa." Would this be too creepy? This isn't a family I know really well, but I've heard about some of the circumstances through the grapevine, and they're really tough.
Alternatively, they attend a church, and I could approach someone in the church office and ask that they be the intermediary, though I don't know anyone in that church office.
Any thoughts about which would be better?