I think it's good to remember that "progressivism", at least as it exists in the US, is not a left-moving political force, but a cutout of liberalism designed to capture anti-capitalist and anti-imperialist (left) political movement, and push them back into liberalism (right). It's structured to be a specific counter-force to socialism. Progressivism offers superficial appeasement on a variety of humanist-sounding issues which are not in conflict with the interests of capital (until they are). It is one half of the culture-war treadmill that redirects people's political energy away from addressing their material conditions and onto cheering on rainbow capitalism and voting for liberals. Reaction with cute stickers.
As much as you think you're trying and failing to move your friend left, they're also trying and failing to move you right.