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I have always gave off a player vibe, is that a good thing and if not how do I get rid of it?
Yes it's a good thing. Every woman wants a bad boy that'll be good just for her. They want a man that's in demand and can "have any woman", because that's essentially a compliment to their own self-worth.
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I never smile is that a good thing (smiling doesn't really go with my personally)
How can never smiling be a good thing? and how the fuck can it not go with your personality? are you some kind of emo goth kid?
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I attract head cases, never really notice it but basically that's all I've dated, is it me or am I really unlucky?
You attract what you are.
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I'm setting up a dinner soon and one of the females I've invited likes me (I think). But her sister and I have a past and it ended badly. I was planning on being nice to everyone at the dinner and just paying more attention to her and notice her a little more than the rest of the people. And if she shows signs that she likes me. Talk with her after, is this a bad plan?
Or you can just flirt with her and not hind behind your intentions.