Are you unscrewing the nut all the way and pushing down on the valve to release a little bit of air first? Also, I have to make sure the pump is pressed down over the valve pretty firmly. Otherwise, the air just sort of leaks out.
And it's not a stupid question. Lots of people struggle with Presta valves.
Live with intention. Walk to the edge. Listen hard. Practice wellness. Play with abandon. Laugh. Choose with no regret. Continue to learn. Appreciate your friends. Do what you love. Live as if this is all there is.
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