Reddit's community /r/agedlikedmilk represents that awkward feeling we all get looking back on our cringeworthy younger selves or past stupid mistakes. This, however, is much more embarrassing or ironic than that sparkly My Chemical Romance crop top you wore in that one awful school yearbook photo. These images said something important at the time, something that is no longer valid.

Whether you're hanging out with Bill Cosby or simply making an offhand comment on a video, these things turned more than a little sour over time, and now they're pretty embarrassing, frustrating, or somewhere in between, especially for the people behind them. Not everything gets better with age, and nothing you find online ever does. But some of the worst of the worst are the images that became horribly outdated by 2022, and honestly, they're just as funny as they are sad. These are 20 of the best images that aged like milk rather than a fine wine.