32 Things Most People Did 20 Years Ago That Make Us Cringe In 2026
Twenty years ago I was just getting into my 20s, which means I spent a solid chunk of the mid-2000s doing all kinds of things I thought made me look cool at the time.
Frosted tips? Probably. Chain wallet? Unfortunately yes. Going out every night fueled entirely by energy drinks and bad decisions? Absolutely. Looking back now in 2026, a lot of that era feels deeply, deeply cringe, but in a weirdly nostalgic way.
The truth is every generation has stuff that ages horribly. Ours just happened to be documented online in low-resolution digital camera photos. Here are some of the things we all did 20 years ago that would make most of us cringe today.
1. Getting an iPhone simply because of the app that made it look like you were drinking a beer.
2. Or the one with the lighter.
3. Posting the most boring updates on Facebook.
4. Or being just a little too intense.
5. When we all thought Chuck Norris jokes were the height of comedy.
6. Somehow watching movies on the tiny iPod nano screen.
7. Typing like this because you were cool and edgy.
8. Or randomly adding Zs to wordz.
9. Taking group pictures like this because you and your friends had similar shoes or bracelets.
10. Why was arguing over who would win between ninjas and pirates a thing?
11. Harrasing Facebook groups with these.
12. Ugh, and the incessant Farmville requests.
13. Faking people out with your voicemail message.
14. Talk Like A Pirate Day was a real thing we all did.
15. DRawing on your Converse and having a little photoshoot.
16. We all did it, and it didn’t look as cool as we thought.
17. When people would insist BlackBerry was way better than iPhone because of Brick Breaker and BBM
18. Watch movies on portable DVD players
19. Using the awful photo booth filters.
20. Change your age to 99 years old on Myspace
21. Doppelgänger Week on Facebook
22. Publicly putting friends on blast was a thing.
23. We were all excited to get that new white MacBook that was filthy after only a week.
24. Wearing shoes that you could also curl up and take a nap in.
25. Update Facebook from the tiniest phone screen.
26. The original selfies with a giant digital camera.
27. When we all thought 3D movies glasses were also a fashion statement.
28. Change your profile pic to something like this…
29. Think adding a “xXx” to a screen name made us extremely cool.
30. Upload 400 pictures to Facebook at once in an album.
31. Spend money on ringback tones. Remember when phones rang?
32. Just…why?
