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I don't really understand where this whole 'league' thing came from in the first place. We're not talking about baseball here. I'm assuming your friend isn't trying to date A-Rod.
You like girl. You want to do naughty things to girl. You talk to girl. Girl talks to you. You ask girl out on date to determine if she wants to do naughty things to you.
Honestly. It's that simple. Your friend has nothing to lose by making a move, and you'd be doing him no favours by trying to convince him that he's not good enough for this girl.
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I wake up in the morning more tired than before I slept
I get through cryin' and I'm sadder than before I wept
I get through thinkin' now, and the thoughts have left my head
I get through speakin' and I can't remember, not a word that I said
- Ben Harper, Show Me A Little Shame
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