I've gradually started getting over my similar feeling-like-a-dick sentiments. I definitely always have the worry that it's not going to work (Google Pay for me here, though), and occasionally I'll fumble to hold my phone in exactly the right way for the particular card reader I'm presented with. I still also feel like if I hand a card to a cashier, and it isn't working right, I implicitly blame the store or their equipment, where if I can't get Google Pay to work, I blame myself, and then feel bad for wasting other people's time.
I tried to use Google Pay (back when it was Android Pay) at a Cumberland Farms and when the reader read my phone it actually crashed the payment system.
A few months later my grocery store put up "now accepts Android Pay" signs. I went through the self checkout lane and the phone was read, but the payment never went through. Had to use my card eventually.
Then my expensive phone broke and I bought one without mobile payments.
But it did work at Dunkin Donuts a few times, so there's that.
