I spent the night in the same room with my guy friend (that I kind of dated for a little while but it never went anywhere) and he wore his underwear to bed. (Tightie-whities). He knew we'd be in the same room so it wasn't a surprise or anything (like he didn't have a chance to bring shorts or something.) I get that a lot of guys sleep in their underwear, but I kind of wonder why he let me see him walking around like that? I could see everything! Did it mean something do you think or was it no big deal? (I wore pajamas and definitely wouldn't walk around in my underwear in front of him. Unless I wanted something to happen, that is!)
Well, I don't know for certain what the underwear was about, but things have changed and we're definitely a couple now! (Not sure that should be a dating strategy though!) All's well that ends well.
I wouldn't walk around my room in my underware with just any girl watching. personaly if I was in my boxers I would get hard just thinking about a chick seeing me in my underware. that and knowing there's only one layer between me and the open air.
so I defnatly would only walk around in my boxers if there's a cute girl I want to try and get with.
I don't know, I've had my guy friends drop trou is front of me... granted they wear boxers. I think widy whities are a bit more "intimate". Guys sleep in their underwear, I wouldn't think much of it unless he attempted to get fresh WHILE only wearing the underwear.