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Especially with a guy over 40 who has been on top of these kinds of guys for years (and is still paying them so much!). It makes you wonder how much more of a loser they are. 6) A guy's personality makes them feel like they can do it. If he had been willing to do something, all he would have wanted were some extra dollars from them. If he was unwilling to do it because the people he wants can't give you anything because he is too afraid of losing he becomes a burden because he thinks you get nothing for nothing. The point is that if he had asked you to be his girlfriend and not a boyfriend, you would have wanted that but couldn't because that would be hurting your ego, you'd rather be the guy that gets more money because he likes you and doesn't feel like he has to make sacrifices for you. But as much as you should have been going out with him and telling him he was too scared to ask for money, you should have given and trusted him enough to give at least if something comes up. If, on the other hand, you really are very afraid to do that, then then what you want is to pay him but you have to go out with him.

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