Would this bother you?

[Ribenafan98]

If you went to a shop with someone and they asked if you'd brought money and you said yes and then they had intended on paying anyway. When I asked, the person said that sometimes I didn't bring money so they just wanted to see if I had. I feel like it implied that Im tight with money or a sponger. I always pay my way with everything so now I'm racking my brain to work out why they said it but they just kept saying they didn't mean anything by it.

That would definitely annoy me! Why are they asking if they want to pay?! I would make damn sure I never let them pay for anything again!
That said, what's the context, OP?

Do you always use card?

What a twat. I'd be distancing myself as clearly either you are tight and don't realise it or they are a big head showing off that they have paid in the past

Why did they pay?

After that comment, they had my item in their hand and put it on the counter and started paying the shop keeper. We bought a very small item each, it came to a few pounds. I should have just said I'll pay for mine but it all happened quite quickly and as they were already paying the shopkeeper and there was a big queue behind us I didn't want to make a scene/fuss.

That was my first thought so I asked "do you feel that I dont pay my way or that you pay for more things or is there an issue here?" They insisted there absolutely isnt an issue.

Do you often let others pay for you?

No not at all which is why im confused and asked the question outright.

Hmmm, all sounds a bit odd then.

Really odd. I suspect there must be more to it and can only hope the person speaks to me about it instead of being passive aggressive.

There clearly is an issue or it wouldn’t even have occurred to them to say something. Either they think you’re taking the piss or they enjoy playing Lord or Lady Bountiful and they want recognition of this because they don’t feel like you’re being grateful enough. Going by how they worded it, I’d suspect the former.

In your shoes, I’d never let them pay for another thing of mine ever again and, if they did, I’d be pressing the money on them. It would definitely change the nature of the relationship. I wouldn’t feel at all at ease with them.

the person said that sometimes I didn't bring money so they just wanted to see if I had.

do you always have money or a card with you? If you always pay your share why would they say you sometimes didn’t bring money? If you always have a way to pay with you and pay your share I would of asked for an example of when I hadn’t paid my way

Are they generally a very socially awkward person? The whole exchange seem very awkward and odd and I think I’d have just been confused rather than upset or annoyed

Hmm not sure about this.

Why did you allow them to take your item to the till if you intended to pay for it?

Not sure how 'quickly' that could've happened really.

And if you always pay your way, why would they say that you sometimes don't?

Are you being completely truthful here?

They can be a bit challenged socially, sometimes say the wrong thing. I was left feeling confused.

Yes I am being truthful, thank you!

They got two items off the shelf which were the same thing, one for each of us. We were in different parts of the store and then met at the till