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If your date loosens up and regains his confidence, that’s a very good thing. Here’s a great rule of thumb – if you feel compelled to talk about your exes, you are not ready for dating. If he starts bad-mouthing his exes, that’s a huge red-flag. Don’t ask about his past relationships and deflect any questions about yours. Should you find yourself becoming attracted to the guy, you’ll be giving off signals that you think are obvious. The guys who pick up on those signals easily are very likely players and/or serial daters.