He seems to like you. I would go after it. I don’t run on a regular basis but for a period of time I ran with a girl I liked just to be near her. If he doesn’t run then this is a perfect opportunity to get a sense of if he likes you. Also by asking him to run you can form a special sort of bond. It will be your special thing together. Even if you stay just friends it will just be your thing. You can compete with him (if he is competitive) get to the top of the hill and just enjoy the view. I would totally go for it. Also, the more time you spend with a person the less nervous you will be around them later. When running simply ask questions and let him do all the talking (plus he will get tired faster and you can beat him to the top of the hill). This way you won’t have to talk as much. Go for it. See if he is up for it. If he says yes it will be fun and you will get a sense of where you stand in your relationship. If he says no, then again you will know more information about your relationship. Ask him. Hopefully he is up for it and you can have a good time.
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I have always found running with girls annoying because they can't keep up. So ask him for coffee
go for it, that's something I have asked my good guy friend to do.
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I see nothing wrong with that, but make sure you let him know your intentions so he doesn't feel lead on.
I used to run with a girl, who asked me, and she made it clear from the start it was purely for company and security.
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