From WWII to us getting humped by petting zoo ponies, our grandparents' "Greatest Generation" witnessed a lot, and as a reward deserves some loving correspondence -- unfortunately, our Shaftest Generation is too lazy to write it. Get someone else to fulfill your duty, with Letters-From-The-Heart.
Started by a West Palm Beach woman who, while working in nursing homes, recognized a need for mas correspondence, LFH provides the elderly with monthly hand-written letters from a "family friend" -- the idea being they'll enjoy hearing from anyone, much like you enjoy receiving naughty email solicitations from...anyone. Register online and fill out a questionnaire about your senior's life: family history, schools, jobs they've held, religion, pets, and interests from film and music to areas you couldn't possibly speak knowledgeably on, like gardening, birding, and Calvin Coolidge. LFH then sends an intro note asking permission to correspond, explaining they're a friend of the family who likes to write; once acceptance is granted, they'll use your provided info to craft a year's worth of personalized letters, plus birthday and holiday cards with corresponding gifts from ornaments to biscotti, but never slippers, bathrobes, Efferdent, or other gifts that make people feel even older.
LFH corresponds with everyone from the spryly lonely to those in care facilities, but will not send notes to inmates, still doing hard time for their own Pony Express shakedown.