Does it matter who pays for what?

So my boyfriend and I have been a little over a year and this year we decided to go in on gifts for our families. I mentioned to him that I would pay for my family and he would pay his half, then he would pay for his family and I would pay my half. So recently we talked about going Christmas Shopping (which we ended up doing) he said we would talk about how were going to do it, so when it came to paying I said I can pay you in cash and then you can pay for it, he was hesitant to buy it so i ended up paying for it and was $2 short. He seems to be a bit short with a couple things, yes its not much but it will all add up in due time.

Yes it does matter
No it doesn't matter
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Does it matter who pays for what?
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