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What was the hardest thing you ever had to tell someone you loved?

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Spn - My "friend" still owes me money, and he would never give me it, even after me letting him sleep on the couch, even after wiping up the puke from the couch, even after wiping it off the floor after he went home. Never loan people money, always take money in advance... I'm not upset about it haha, it's just a valuable lesson.