How to advance in a relationship?
I came from a very poor family (absent and financially unsupportive father, mother working at or near the minimum wage while raising two kids) and my sense of values reflected that situation. Whenever I received a gift from someone, I would end up either feeling guilty because I thought they were wasting money on me that could be better used elsewhere, or else I worried that I was somehow abusing the relationship and allowing myself to be "bought" (although for what purpose I couldn't tell). I simply couldn't understand that their perception of money was different from mine and that what I saw as a lavish gift was a minor expense for them. (Mind blindness?) As an adult I stumbled into a high-paying career, and suddenly I was on the other side of the issue. Now there are occasions where I want to buy someone a gift they couldn't afford on their own and the situation becomes awkward for all the same reasons. In each case, I have to convince them that (1) the gift is given out of a sense of affection, not a sense of duty, guilt or pity; (2) there are no strings attached; (3) it will not cause me any financial discomfort; and (4) I'm not doing it simply to impress them. Once they accept that my motives are pure and my feelings are genuine there's a lot less resistance.
If there is a serious disparity between your financial situations, you would probably be well advised to stay away from lavish gifts (from your partner's perspective) until the relationship is well established and your partner has acquired some comfort with your financial situation. IE: If your date's finances are such that fast food is a luxury, then you want to skip the better restaurants and stick to McD's for a while.
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What would Flying Spaghetti Monster do?
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