When is it appropriate to approach a guy a second time?

Situation in short: he says he wants to hang out, several times. When I finally get the opportunity to talk to him he ditches after a few minutes. A bit later, maybe ten minutes, he's alone so I go talk to him again. Within fifteen minutes he's off, without me even talking to him because I had an urgent restroom need and had to leave him with my friend.

I think he thought I was trying to set him up with my friend, which I wasn't. I'd like to try approach him again without her, see what happens, but I don't know if I should wait for him to come talk to me instead since my second try was such a blatant fail! What's the social protocol for a situation like this? Next time I see him and I'm not with my friend would it be weird for me to go talk to him?
When is it appropriate to approach a guy a second time?
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