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And remember, it's kind of sexy when a man feels empowered enough to discuss his feelings.

At first, he may be quiet and always ready to give you advice when you need it.[Read: How to deal with insecurity in a relationship] That’s the strange power of insecurity and insecure men in a relationship.Experiences with insecure men The first time I ever dated an insecure guy was almost a decade ago.Do be understanding I can get kind of defensive when dating older guys, worried that some might see me as another notch on the bedpost, or fresh meat to pass the time until someone more serious comes along.She may be younger, but her feelings are just as genuine as yours. Do establish boundaries In some rather obvious ways you’re at different stages of life, so if you're just enjoying a fling make sure she isn't shopping for wedding dresses.