I was thinking leggings and this red plaid flannel shirt. Chances are I'll end up sleeping in it, so I don't really want to wear jeans and/or a sweater. And last time this guy came over, it may have been bc we were both nervous but it was super hot in my room, so I don't really know what's a good plan. Any ideas would be greatly appreciated!
Leggings and t-shirt, if you get cold you can always grab a blanket or put on a sweatshirt. It's a little less awkward and less suggestive than if you were to get too hot and sat there unbuttoning the flannel to take it off. Dude might get the wrong idea, unless that's the idea you want him to have.