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Dear So boring,
It sounds like you've got an expert in talking to guys, right there. So take advantage of her expertise! When you are hanging out alone with your friend, talk to her about this problem. Tell her that you feel boring around guys, because you never know what to say. Ask her to give you her best tips, so you can become as outgoing and friendly as her.
Then, and this is crucial, ask her to "help" you to practice. Say something like, "Hey, let's try out my new skills on that guy over there. Will you come with me and just hang back without saying anything for a bit, to see how I can do?"
