I wear mainly boxer briefs - I wear boxers too, but mainly to bed so they're more like pajamas to me than underwear. I think my most awkward underwear-related experience was when they were giving Carlton Dry boxer briefs away at work with every carton of Carlton Dry we sold... so we had to ask all these men (mostly middle-aged men, too) what size they were. So damn awkward. But it led to me getting like 7 free pairs of them at the end of the promotion because we didn't get rid of them all :P
This sounds bad, but my mom deals with all the laundry stuff, so my underwear is pretty much her domain. I just fish them out of the top drawer of my dresser as needed. They're always folded though, even though I don't really see the point. I guess it keeps the drawer neat, but it doesn't need to be folded for the sake of the underwear itself because unless you're planning on undressing in front of people nobody is going to see them lol
I guess in total I'd have about 20 pairs of underwear, give or take. I'm too lazy to go to my dresser and count them, and some would be in the wash anyway.