Paying the bill & confusion

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    I was dating a man and he recently circled back into my life saying he was foolish, was being immature and made a mistake. He realizes now that he wants me.

    We meet up for drinks and I let him know that I wanted to hear more about what happened the first time. He proceeds to tell me that I have the whole package of a good woman but what bothered him is that he always paid.

    My first thought process was he has way more money than me. Next I thought he always asked me out knowing I am a single mom, just divorced, student (PhD), and work for 2 nonprofits. Then recalled with all that in mind I never always expected him to pay. There are several times I offered and genuinely was willing to pay because I did set aside a little for our date. Everytime I offered to pay or split the bill he said a firm no.

    So I would do other things like drive us there or try to pay for the little things (like water if we went to a club), Pay for a date I found in Groupon that he mentioned he always wanted to do. Buy a round of drinks here and there. When I mentioned all this to him (offering to pay, buying small things, paying for an occasional outing) he was like “I guess you kind of did do that”. I also reminded him that I took him out to a very expensive steak dinner because I wanted to treat him. That night I told him you are good to me and I want to do something nice for you. That was our last date and we stopped talking as much. He also started dating other women rigt after that.

    When I asked why he did that, he said it made him feel some type of way. I told him I see more than just money when I am with him. We laugh and talk for hours. We have fun. He agreed and says he wants a women that can afford to do more, even if it’s just paying for small stuff. I told him I can continue to pay for occasional things and small stufff. If he wants me to pay more we cannot go to $300 restaurants and he cannot get upset if I pay. He said “I know, I think you need to be more pushy or just add your card. This is something I am working on”. I explained you are an Alpha Male, me paying might hurt your ego and cause drama.

    I told him to think about what we talked about and we went our separate ways. He text me this morning and wants me to go to a place where I will meet his sister. I wake up pissed and hurt by our conversation last night.

    Why is it hard for him to see the little/small things I did do? If I do pay, what are the chances he will freak out again? Is this guy just a jerk and I should move on? Or am I being defensive because my feelings are hurt?

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