Perhaps I was not clear…I did think it was a good idea to remain discreet, but discreet does not equal anonymous. What I suggested should be said privately with no one else to hear but I do still think the original poster should say it in person.
I am not an advocate of anonymous emails or letters. If someone sent me something horrible about my husband in an anonymous envelope or email…my first thought would be to think it was an ex-girlfriend being nasty and I would be suspicious of it’s validity. However, if someone came up to me and said “sorry to hear…(blank)…I will pray for you” I think that would be charitable.
If this poor woman gets an anonymous letter she will wonder her entire life who sent it which I don’t think is nice. The anonymous approach is nice for the original poster of course…but the recipient will wonder who is digging into her business and she will always wonder…talk about paranoia! Let’s face it, there really is no easy way to approach this situation.