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Damon hasn't seen how Jo and Alaric are together, though. He wasn't there during their "meant to meet" conversation, he didn't see how desperate Jo was to save Alaric, and he wasn't there when they were all cute & fluffy on the coach. I agree with Anna, Jo and Alaric are already falling in love with each other.
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Damon was there when she was saving him though at the border and with his vampire hearing he must have heard everything she said. I just think he probably thought she was in her doctor mode so he didn't take her words too seriously.