I just think of it like this: If you died tomorrow, would you, theoretically, regret not telling him you had a crush on him? If the answer is "Yes", tell him. I had a similar situation recently where a friend-of-a-friend messaged me one night. I just told her I've had a crush on her for years and we're going on a date next weekend.
If you don't ask, the answer is always "No". Remember that.
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Why not think about finding a song or article that you're interested in and think he might like? Then you'll have a reason to talk to him and something to talk about.
Duh! And you say you are not naturally boring, I can relate, You'd be amazed the kind of confidence you will get hiding behind a screen
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Don't try the private message cause it always goes to the other folder and the last time i read one was after half a year so message him after he accepts your friend request. Send a request again just to make sure he recieves it And best of luck !!! ^_^
I think you should do it
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