Too shy to talk to a girl you're interested in?

(Below is background, but I basically just need advice on how to get a fairly shy guy to ask me out)
So there's this guy I've been pretty interested in. We've hung out in a group of 4 (me, him, and my friend and her boyfriend) twice and it's been a few weeks since I've even seen him, but my friend and her boyfriend are definitely pushing us being a thing, and he apparently is interested in me (according to the boyfriend, a good friend of his). The issue is that he's pretty shy and told his friend he's not as smooth as he used to be, so is afraid to talk to me.
I just feel pretty bad because I really do like him and he wouldn't need to be smooth for me to talk to him! I get that I might be considered conventionally more physically attractive than him, but he's very talented and sweet and if anything I'm in intimidated of him!
So, long story short, what can I do to encourage him to maybe ask me out?
Too shy to talk to a girl you're interested in?
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