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I don't think it's too weird. Lots of girls have guys like these (your friend in this case) as a backup, bro or a shoulder to cry on. I would let your friend know to stop wasting time here because time and money is precious. You can make money back, but you can never make time back.
In this situation you've provided I cannot critique the actions from your friend. But what I evaluate from this is that he 'friend-zoned' himself. I THINK (again I don't have the proper information I'm making assumptions based upon information provided) that he took way too long to try to make a move and if he just found out that she has a boyfriend now, he obviously didn't pop the question or even ask intimate questions like "are you looking to date now?" or "what type of guy are you into?".
Remember, to get the aces and kings in a deck of cards, you just have to keep flipping them.
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