What does it mean if a guy hangs out with a female but constantly asked why she is with them, mostly because of their lack of money or resources to take the female out on nice dates and stuff? Even when she has explained more than once that it is not about that, he still make comments about how she should be with someone better, or that he doesn't have enough for her. But he still wants to hang out and see her, and he makes comments that he likes that other men admire her. Is it stupid for a woman to stay around, even if she somewhat likes the guy. Is he trying to push her away, or is he just insecure?

I would not stay around. If the guy cannot accept or understand that the girl just wants to spend time because she likes him, then the girl needs to find someone else that does not question her motives all the time.

It sounds like both, or he is just looking for someone to tell him that he is important. Im sure he likes you, how long have you been seeing each other? My boyfriend does that to me, because he doesn't have a lot. He is always asking me why? ANd I just tell him because I love him. Because the finer things in life don't matter, because if you care about the person that much to still be with them, they are the finer things in life you know?

I agree, and I have explained that. He says he's insecure, I say you don't need to be. We broke up because of this issue the first time. Now we're friends and we'll go along along fine, then he'll ask why haven't I met someone yet that has more? It's like he messes up a good time with questions like that, and I start to feel a little unwanted. Now I just answer his questions honestly( about other guys and stuff), because I feel I've already told him that I like him and the other stuff doesn't matter.

I've been hurt a lot myself so I'm still a little sensitive to not being sure if a guy really wants to be with me, so I guess that is why I am confused. I want someone I can be comfortable with, and I am with him... until he starts talking that stuff. It makes it hard for me to get close to him. We haven't even slept together yet. I've known him for about 7 months now.

Does he feel the same way as you do? If so then you need to talk to him about this. Tell him excatly how you are feeling. Tell him he doesn't have anything to be insecure about.