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I, too, find the subject fascinating, but I find many of the books overwhelming. One of my problems is that I have the long ingrained habit of reading one thing at a time, and philosophy tends to be too dense a subject for that to work very well (you don't get the best out of the book, and it still takes a very long time to get through it).
I recently read "Every Time I Find the Meaning of Life, They Change It", by Daniel Klein (2015). This is a very light way to get a peek at many different schools of the thought. In some respects it's too light, it often leaves you wishing for more depth, but because it is this light it is more accessible than many other works, and it gives you enough that you can go looking for more on areas of interest.
Another fairly recent read was "Unto This Last And Other Essays On Political Economy" by John Ruskin (1862). Difficult, but I found it to be a rewarding read. I have studied some economics and accounting, and it was interesting to find a contrasting view of how economics might work - one based on an entirely different philosophy. (I came to this after reading that Gandhi was influenced by the "Unto This Last" essay, which I found intriguing.)
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The other thing I might suggest is that many readers are closet philosophers, whether they realise it or not. One of the joys (for me) of Terry Pratchett's work are the deep thoughts that lie behind the humour. And I'm currently reading "Lamb" by Christopher Moore, which is as funny as I expected but also much more serious than I expected - often in the same line. The book is much more thoughtful than the tagline or blurb would have you believe. (I suspect this talent is why I've seen Moore compared to Pratchett.)
It can be easier, more accessible, to be confronted with the big questions in a narrative - something that Plato tried to achieve with his dialogues. ... Of course, the reader is subject to the whims of the author in this case. (This is partly true in dedicated philosophy books, too, but in a fictional narrative it is easier for the author's whims and prejudices to hide behind the dictates of the story.)
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