If he knows she likes him why won't he ask her out?

because he doesn't see it as a challenge anymore * He may be shy or tongue-tied. Test by you asking HIM to accompany you somewhere-- make it an easy place to go that won't cost him money more than his usual expenses, like lunch together at the cafeteria (Dutch treat) or someplace that is on HIS way home. If you force him to talk to you on your psuedo-date, you will be able to tell if he has an interest. (The clue will be that he does talk back to you and he doesn't try to get away from you 'as quickly as possible'). * He may view you as a thrash toe. If you were 'going out' with Bob last week, and Bill the week before that and Frank the week before that, etc. he may be correctly seeing you for the opportunistic gold-digging user that you are. And he would be the smarter man (or boy) by avoiding you, regardless of how much you want him to 'date' you. He may not want to be the next victim (sucker) of your greedy 'dating game'. * He may not actually 'know' that you like him as you think he does. Making assumptions about what someone else "knows' or doesn't know is not appropriate. Frequently, our assumptions are wrong. You can test this quickly and easily by walking right up to him and saying, "I like you- you wanna go out?" * He may be the Mac-Daddy player, gleefully thrusting his way through the flower-bed of better pickings right now. When he's done doing those he perceives as more desirable than you then he'll approach you, all lovey-dovey, with sweet-talk about how all those other girls meant nothing to him and how he was foolish for not seeing your great beauty and love before now. Of course, he'll fill you with platitudes about how smart you are and he'll make you feel real good when he tells you that you are 'different' from all the rest. (Joe snickers for some unspoken reason) * Finally, he may only be looking at the outside. You may not be his 'type' (visually). Unfortunately there will always be many people who look only at the outside, violating the maxim to not judge a book by its cover-- the type of people who think the phrase "Beauty's Only Skin Deep" is just the name of an old song by The Temptations. Alas- sad but true. The only consolation we have for those type of people is the knowledge that many of them will end up in heartache producing relationships themselves (See 'Thrash Toe', above)