I also prefer not to share rooms if I can avoid it. Sometimes out-of-town family events just demand it or other things you can't get out of it. I recently had to share a room with a cousin at a big family wedding we were all at. Since I don't share a room very often, I wasn't even thinking when I packed and didn't pack any boxers to sleep in (I always go commando), and got a little uncomfortable the first night after a late dinner and drinks when we headed up to go to bed.......... then I just thought, 'fuck it, I'm 40+ years old and if Marc (my cousin) has a problem with seeing me naked it is high time he got over it'. So I just showered, came out of the bathroom in a towel, sat on the bed for a min or two, then just pulled it off, ran it over my nuts a couple of times to get em good and dry and stood there nude as I pulled back the covers to get into bed. He just looked at me, a little surprised I think, but said nothing. He had already gotten into bed in his briefs. Interesting tha the next night he took off his briefs to get into bed and made the comment, "I usually prefer to sleep naked also, glad you don't mind"........lol. Then the third night we ended up with his father having to share our room because the hotel was full and he arrived without reservation. So Marc sleeps on the sofa bed, his father in the other bed, and here I am dealing with the awkwardness again with my 60 year old uncle now in the room............. turns out it wasn't a real problem because he stripped down buck-naked before any of us and was walking around so clearly sleeping naked wouldn't be a problem.