A true friendship always comes back no matter how much a heart is broken. So talk to him about whatever you did (or said to him) whatever happened. And just simply explain to him that you truly are sorry from the heart and truly mean it

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I have but this isn't the first time I've done it this is the fourth time I hurt him...

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Then give him time to cool down and see if he re-starts the friendship again on his own terms with You. You don't want to keep pushing things. As tough as that may be to do is wait. It's the only real other solution

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