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So if I can talk about this with dudes, anyone can. Like I said, this might be a slightly awkward convo – there might be no getting around that. Would you rather be lame and sit around waiting to hear what he thinks or would you rather take the initiative and find out where his head is on your own? Here’s what to do: first of all, this conversation should happen in person, not through text messages, Facebook chats or even on the phone.