I may not be able to help you so well cause these are people I don't know, but it may help with you decision wise that is.
Anyways, if I were you I'd just answer these simple questions like do I just like this person as a friend or more, will I regret doing this, would it be right to, and so on.
If answering those questions doesn't help then let me explain in my opinion. You said how someone said that if you made him wait longer he would end up asking Olivia and that he just liked her as a best friend. That right there is the key clue. If he doesn't like her more than a friend he would never ask her, so now he is just waiting for you. If he really likes you, he would wait even more despite that fact of the past waitings.
Also, don't go with what others think and even my opinions too if you want. At times they can bring you down even more and make you feel terrible, so just believe in what you think and not just others.
In the end, just follow your instincts and trust in yourself and others around you is all I can say. If I knew these people more and the situation, I'm pretty sure I could have helped you more. Sorry and hope for the best on your decision!
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