Is AUTHOR wrong in the post ? POST : Disclaimer(s): Suck at English so any poorly worded things I can elaborate on in comments. Also, highschooler so a pretty dumb situation anyways, lol. 
So, for about the last year my friend has been interested in a girl we know. He asked her to homecoming last year and this year and she said yes, but last year's spring dance she said no. From mutual friends I have learned she has no interest in him and he knows this himself, but he continues to chase after her. She's too nice to say she isn't interested in him to his face and his sisters are friends with her so, yeah messy situation.
He wants to go speak with her when he gets the chance and I always encourage him to do so, but he never does. I feel he squandered his chance for anything meaningful with the girl because he never really committed to forming a real friendship with her.
I've always stepped aside when I've learned that my friends have feelings for the same girl and tried to be a good wingman, but this time I want it to be different. I value my friendship with this guy though, but I also want a meaningful relationship with this girl too. I feel backed into a corner where I lose no matter what route I take. So, I'm asking WIBTA if I started chasing this girl either while he's interested in her or after he loses interest?