You need a second friend ... "C" ... to make it easier ...
In these kind of situations ... a second friend, person I will call "C" could be of great help.
"C" should be someone who knows both of you, "A" and "B"
You are "A". The guy is "B"
"C" should contact "B" and find out what "B" thinks about "A".
If "C" feels that it could be OK (it seems that "B" also likes "A"), "C" may even suggest to "B" that "A" likes "B", and that "A" wouldn't mind if "B" would more often invite her out ....
"C" type of people are great to help to people like "B" or "A" to come together ...
when both "B" and "A" are too shy to move forward without some help ....
There is also another possibility!
"C" may also find out that "B" is not all that much interested in "A" (unlikely)... and in that case ... "C" will just give a message to to "A": move on, "B" is not for you!
yours truly
"W"