When you lose this confidence usually you start to lose communication. You start assuming things which aren't true. This is where the danger lies. Its good you are keeping communcation open, and he's having a positive response to you. You haven't told us about your past so I'm not sure what we are dealing with.
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This would irritate me a lot. Why does she want to be friends with him anyway? Particularly since they weren't friends while you were dating.. from the sounds of the nature of your friendship it seems like they are BOTH trying to make you jealous. She must know that it bothers you, but does it anyway because she enjoys the attention and competition and knows you won't say anything about it. He probably likes the ego stroke that your best friend talking to him gives him. If you are such good friends you should be able to tell her how you feel. There's no point keeping someone in your life that ignores your feelings and/or deliberately makes you uncomfortable. Not to say you should ditch her AT ALL, those long friendships are very important... but you can change the nature of the friendship by dropping the competition and trying to support and comfort one another instead...
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