Yes, I think that might have worked. I could see Dana being a friend of Lisa's but having a crush on him. She wouldn't be the type of girl to try to break them up, but if they broke up, and Casey started being charming to her (as we know he can), I can see that happening.
In S1 she mentions that he did it in college, in Texas and in LA (in that order, oddly enough), so it does seem to be a force of habit.
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Yes, I think that might have worked. I could see Dana being a friend of Lisa's but having a crush on him. She wouldn't be the type of girl to try to break them up, but if they broke up, and Casey started being charming to her (as we know he can), I can see that happening.
In S1 she mentions that he did it in college, in Texas and in LA (in that order, oddly enough), so it does seem to be a force of habit.