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How to move forward financially with this person? 19.1.3>46

heatwave

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I've been seeing someone who has paid for almost everything for all of our dates. I didn't mind allowing him to spend the money at first knowing that this is one way he was sort of wooing me. Not to mention he makes substantially more money than I do and has a fraction of the bills that I do. That part doesn't actually matter to me though. Mostly I just know he is a traditional guy and have been along for the ride of letting him express his attraction by taking the lead. I'm now starting to feel like I need to contribute more. It would feel odd at this point to offer to split the check at the end of dinner though. Maybe I shouldn't be giving this so much thought and just offer. I thought our date tonight would be a good start because I could just buy the tickets in advance and let him know when we get there that I already bought them. I consulted Yi about whether I should buy them and got 64.4>4.

I'm kind of embarrassed by this question. In the past I have always made an effort for things to be more equal and now it feels strange to start asserting myself not from the beginning. 64.4 was off-putting somehow. Like going into a battle with power dynamics or something that might eventually even out but would not be fun in the meantime. So I just asked the more generic question of how to move forward with this person financially.

46 as the context of my question feels like exactly what I am asking about. Taking small steps to ascend in the relationship. I've also seen this pop up for me when things are growing or changing very slowly, for example when asking about a friend's broken bone taking an extremely long time to heal. 19 can be like that too, like things are advancing gradually. So what of 19 here? Should I, for example, offer to pay for drinks at an event he paid to go to because it is a natural place to make an offer? I wonder if the complacency in 19 is me letting someone pay for everything. I don't need things to be perfectly 50/50 in this realm. I bring other things to the table. But I want to show my appreciation and generosity in a more concrete way without disrupting the dynamic in a way that would make him uncomfortable or me unable to accept his invitations because I simply can't afford this much this often.
 
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