I don't want to hurt him again, but at the same time I wonder if we are supposed to be more?

OK so I started to become really good friends with this guy, hanging out every day, and my roomie recommended that we date so we tried it and it didn't really work..well now we have become friends again and I get that weird urge to flirt with him and that I want to be more...I don't want to hurt him again, but at the same time I wonder if we are supposed to be more since this has happened twice...please help
I don't want to hurt him again, but at the same time I wonder if we are supposed to be more?
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