Philosophy is a big broad subject, some of it is hard but a lot is easy. And the good thing is that the easy bits are in many ways the most important bits. One of the best ways to get into it is to follow the route of history, starting at with the earliest philosophers, that gives a narrative structure which is easy to follow if nothing else. I would therefore say that before reading a single philosopher you read a book on the history of philosophy, of which there are many good ones. Then you will know where to go next, if nothing else.

Yes, I recomend starting with a simple primer on critical thinking, buy or download a glossary or dictionary of philosophical terminology and then begin by reading the classical philosopher that appeals to you most, study him or her and then read an opposing opinion from another and another who opposes this one.
You will find a chain of learning emerges and you shall find that you will begin to think more deeply, be more questioning and in time will find you "way" of understanding the world.
Philosophy means quite literally the Love of Wisdom, make sure that is what you want and that you are capable devoting yourself to it before you begin, to start on this path and to stop will leave you confused and unfulfilled, but a life time spent in the pursuit of wisdom is a life well spent.