First up: The sign from the restaurant The Hub and I went on our first date. We went there again on our first anniversary (the little wedding anniversary), and the owner told us he was getting a new sign. Before I could remember to be polite I'd blurted out, "Can we have the old one?" It lives with us now and takes up the majority of a wall.
The next two are pastel drawings done in 1905 or thereabouts. The kids are my great-grandfather's older brother and sister, and the adults are my great-great grandparents. My great-grandmother (the Viola from the story a month ago or so) showed these to me about 10 years ago, then promptly returned them to their hiding spot underneath her couch. When she died, I asked my grandmother if I could take them, and she said, "Oh, of course, I was just going to burn them." There's a bit of glare because I've since framed them, but after playing with the angle it isn't too bad.