The /r/askphilosophy sub is pretty great, lot of very knowledgeable users there, similar to the /r/askhistory sub

I wouldn't recommend starting with Kant, but if you're interested in early modern philosophy to Enlightenment stuff (roughly 1400s-1700's) I'd start with Descartes and work your way from there, he sort of lays the groundwork and context for a lot of thinkers past him. You probably won't agree with him, and almost everyone who responds to him has major criticisms, but it's a pretty good starting point because it's a clean break and highly influential at the time with many philosophers of the era directly responding to his ideas.

Rough sort of cartoon timeline is you have Descartes who advocates philosophy called rationalism, which is advocated and modified by certain people and critiqued by empiricists. Kant comes along and attempts to synthesis both of these schools into one and largely succeeds in doing so, Hegel follows up and radically complicates things but borderline creates a functioning "system of all systems," that is still pretty debated and relevant today. Things are a bit muddier than this, but it's helpful to have a broad idea I find when navigating this stuff.

This is also a highly useful website as well: https://plato.stanford.edu/

It can help with reading and provides pretty broad overviews and introductions to a lot of different ideas and works. Last bit of advice is people on youtube (i.e. "The School of Life" and other such vids), especially highly rated channels tend to be pretty wrong about a lot of philosophy lol, so tread carefully there, although there is absolutely great stuff here and there, it can just be hard to tell the difference early on.

Best of luck!

Nice, it's some of the most rewarding reading you'll ever do, and really helps to complement historical reading too as a lot of these people didn't make the rigid distinctions between fields like philosophy/physics/science we make today. Like reading about the enlightenment after reading people like Kant and Locke gives you an entirely other perspective on the entire era. German Idealism and structuralism ended up being my jam, Kant and Hegel are just once in a generation geniuses, but it's great because the field itself just spills out in so many different directions.

Philosophy is still highly relevant today with this sort of thing, a lot of good philosophy isn't about answering things definitively, it's about formulating the right questions and conceptual ground for discourse going forward, something many technocratic people tend to misunderstand or write off.