Dude, this has been something I've wondered for a long time:
5 Girly Things Guys Really Like
Quote:
I learned this during a moment of necessity: I hadn't done laundry in a while and I got caught short when someone came to the door, so I threw on a University of Texas women's T-shirt belonging to my wife, Karel. It was a little snug, but, wow, it felt like I was being hugged all over by a fuzzy Labrador puppy. Men's T-shirts, by contrast, feel like wearing a layer of sandpaper. In order to get a guy's T-shirt to the standard level of softness and comfort that a woman's T-shirt starts with, you have to work out in it for three weeks straight, leave it outdoors through an entire rainy season, and wash it 65 times. Then you're rewarded with a month of happy wearing before it falls apart.
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It's so true though. My t-shirts are stiff, rough and uncomfortable. On the other hand, my wife's t-shirts are soft and ... well, that's all I know. I can barely keep her from wearing all my clothes, much less ever put on one of her t-shirts. (She's even stolen my socks and underwear! Bet my boxers didn't fit quite right in the front

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So yeah, while I wouldn't wear lingerie, I can see where guys come from ... and I can see where women would think it's weird ... even though she's wearing your boxers while thinking it's weird.