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I think women are smarter than men by always wanting to know where things are heading. Men (young men particularly) don't necessarily care about the future, as long as things are going well right now. There's a lot to be said for going with the flow. It's easier, and one can have faith that if it was meant to be then it would be. But blind faith rarely works. I guess we all have to grow up sometime. Some men wake up during a mid-life crisis, realising that things haven't worked out as well as they'd hoped, simply because they didn't wise up and apply some direction to their lives, but just let it slowly work its way into the toilet instead. I'm convinced men need women, just as much as women need men - we complete each other, by making up for each others weaknesses.
Anyway, back to you - I'd be honest (it is the best policy after all) and tell him that you have hopes for the future and need to be able to see that your life is heading in the right direction. You don't have to scare him off by planning out his future for him, but you can ensure that he, at least, has similar intentions to you. I would hate for any woman to be in a relationship for many years only to, one day, find out that her partner has discovered his destiny, and it's in a different direction to hers. He wouldn't see it as a waste of time, as he got what he wanted out of the relationship, which were the good times spent together (since he wasn't after anything more), but she would, since she probably had their future together all planned out.
With the cheating issue, tell him that his 'ex' is not you, and you are nothing like her. He needs to get that clear in his head, otherwise he will never fully trust you, and when things get tough, like during an argument, he may bring those feelings out and actually expect you to cheat on him, and, worse, treat you accordingly. All hurts and mistrusts like this need to be healed. That's what building a relationship is all about.
Also, the thing about men not talking about their emotions, it's normally because men don't understand them. Given enough negative emotions, and they may also decide that they don't want to know them. I think society has really let men down in this area. It teaches them how to make a buck, but how to form a relationship is something usually left to parents or religion. A woman who subtly helps a man to understand himself is a Godsend as far as I'm concerned, an angel even.
And the right time? It's when you're ready to sort it out - not him. Good luck!
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