He keeps on insisting to pay...should I go with it or fight it?

There is this guy who I guess I am dating...as in, we have gone out on three or four dates, and have both admitted that we like each other. Well, the thing is, every time we go out, he ABSOLUTELY INSISTS on paying. The first date is one thing, I get it, you let him pay. Our first "date" was actually prom, and he covered everything even though the tickets were painfully expensive. I was uncomfortable with it and tried to pitch in, but he insisted. I thought that after a few more dates, the money issue would fizzle out, and he would let me start paying for myself, but it hasn't. I've started getting a lot more assertive about it when the bill comes, but he still won't budge. I know I probably shouldn't be complaining about it, but it just makes me uncomfortable, because I know he works a lot and that he's saving for college..I don't like him blowing his money on me. Should I have a conversation with him about it, like during a time when the bill isn't actually sitting in front of us (cuz he always wins when that time comes), or should I just let it go? Will it offend him if I keep on trying to pay for myself? What does a guy think when a girl tries to pay? Will he eventually start letting me pay anyway, when it's been a little longer?


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Most Helpful Guy

  • I always insist to pay, but I was brought up to pay for the woman. But it made me struggle to afford the bills and my girlfriend found out

    She talked to me about it and I appreciated that she did talk about it, now we split the bill even if I pay for a taxi home or something else

    A relationship is about compromise sit him down when there is no pressure to pay if anything allow him to pay and split the bill afterthe date this way he won't feel embarrassed if he feels awkward having others pay after

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What Guys Said 1

  • He wants to treat you good so talk to him and he might pet you pay a couple of times!

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What Girls Said 1

  • Keep offering.

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