So I am dating a wonderful guy, when we initially met, I had a steady job and we would take turns paying. Over the next few months of dating, I quit my job and became a full time student , which means I turned broke ... My boyfriend has been really generous with paying for our dates, and I pay here and there but it's mostly him, I always appreciate everything he does and always let him know that I do. I really wish I had a job so I could do my fair share and I will when I am done with school in 3-4 months. we were planning to take a trip over the weekend and if he knows where we would stay, I suggested a place and he casually said "you gonna pay?" I know he didn't say it in a malicious way, but I just feel really really bad, somewhat useless at this point... I don't know how to describe it, I have always been independent and at my last job was making a decent amount. And he knows that I am broke so why would he even ask that? I am considering taking money out of my savings to just prove to him that I can pay for it ... Am I just making a big deal? or is this a big deal?
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Under my interpretation, he's saying "Do we really need to go do this" by asking if you were going to pay. Me and my girlfriend just had a similar adolescent discussion a few days back (Hey! I'm still working on listening) and she wanted to go to the coast; I'm a full time student with financial structure and she just lost her job (neither of us have income). So I said something similar to "are you paying"... And the point was that I wanted her to get the perspective that without income, I don't feel comfortable to pursue our dream of "going out" whether to the coast, or across the world, or to a local restaurant. Money means future, without money, I can't buy shoes to get to work or pay for my gas, insurance, rent, cell phone, etc.. So I'm gonna keep costs low until I can replenish my supplies (cash).
It may have been a low blow, and it's perfectly acceptable to clarify the statement: "John, I can't tell if you're being sarcastic or serious.. Could you clarify the point you're trying to make more directly, I think you're worried about funds because I don't have a job and this economy is hard. Maybe we can compromise and put off the trip for a month or two for both of us to save up so neither of us have to worry about it?"