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Why Would He Be Stingy With His Girlfriend?

I (25/F) and Art (30/M)recently broke up from a 1 year relationship. The problem: he barely paid for our dates, even after I told him it bothered me. He wants to get back together, but I'm unsure.

Art is a smart, sensual, and charismatic man. The other parts of our relationship were fine except this. But this issue stuck out the most to me. When we're first dating, Art offered to pay for us. But after we became exclusive, Art told me he hated women who wanted men to pay for everything and thought things should be paid 50/50. So, from then on, we split the bill. It wasn't romantic to me, but I really liked him. After a few weeks, Art complained I never paid for him. So, I did. I either paid for both of us or I split the bill with him. But very rarely did HE pay for US also.

After several months, I got angry. I like simple things. A dinner, a movie, some drinks now and then. But not always on ME! I told Art he was slacking. Multiple times. His answer was either a)total disbelief, b)reassurance that things WERE equal, or c) telling me he'd "look into it", buy 1 thing and then stop. For a while, I dropped it. I hated the negativity arguing brought. I hoped he'd change on his
own. He did not.

I decided to have a conversation about his finances. And Art told me he:
1)was financially ok; pays his bills fine
2)"put the matter into his subconscious" and knows he didnt handle it well
3)was "working on it his own way" but "obviously not the way I wanted."
4)was trying to spend on me and save for his future, but somehow failed to do both and is unsure how.
5) paid for his exs' dates when he earned more,but since he makes less now, he wants to spend more wisely.

Art's now paying for my plane ticket to come see him (My job transferred me to a different state before I broke up with him). Which I find ironic, cause he's spent more on me now that I broken up with him, than he had when we were together. Art wants us to get back together. But to me, if we lived closer together and I told you to step up in our relationship and you didnt...how would it get better, if we're now states away?

And why would a man be so stingy anyway?

Your thoughts?

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