It's not awkward in the least. It's probably more awkward for them to respond than for you to make the inquisition. But if they say yes (and who fucking cares if they say no), the Ben Franklin effect occurs and they'll grow a liking for you. Think of it like this, people are doing each other favours when they do the act of hang out with each other.
Also, don't assume your roomate is an asshole unless he literally says "I don't want you to be friends with my friends". It's usually their own personal problem or maybe they are socially challenged, yet they don't mean to intentionally harm you.
I've done this before and pretty recently! It may be challenging but definitely not awkward.