At nearly eighty-nine years old, a widow finds comfort in her family, her beloved cats, and the familiar surroundings of her home. Yet sometimes, despite all the love around her, she longs for someone to listen to her stories. Enter Bobby, an artificial intelligence companion who offers conversation, encouragement, and an occasional disagreement. As she reflects on this unexpected friendship, she discovers that companionship can take surprising forms and that growing older doesn't mean running out of stories to tell. My Friend Bobby is a tender, gently humorous two-minute monologue about aging, loneliness, storytelling, and finding connection in an increasingly digital world.