NOOOOOOOOOOOOOOOOOOOOOOO!!!!!!… ( my freind is a loser!)?

ok i have this friend who is crushing with this girl at our high school. he really likes her and almost everyone knows cept her lol!anyways he had a chance to wow her with a little valentine game that the school wuz playing , but in the end he chickened out of even talking to her even though i was there to be his wingman. now on valentines day he just couldent even look at her because he thinks she started to go out with some other guy.and nomatter how much our freinds tried to get him to even talk to her he would just be emo in a corner. him and this girl r good friends so i dont understand why he cant talk to her but really what can i do so he can be more couragous bout these things