I don't recommend most of what passes for modern philosophy, because it's more a form of mental masturbation than a means of developing the mind. What I're recommend, if you have no previous exposure to philosophy, is to hit the library and find a textbook or two, the sort that gives a general overview of the history of philosophy and potted versions of what each of the major philosophers taught. That'll give you an overview. Then pick a book or two and plunge in. One that many people like is George Berkeley's Three Dialogues between Hylas and Philonous, which was published in 1713; it's not too long, and though it's written in somewhat old-fashioned prose it's pretty lively. After that, well, there are plenty of choices; I favor Schopenhauer's The World as Will and Representation and just about anything by Nietzsche, among the moderns, and Plotinus and Proclus among the ancients, but your mileage will doubtless vary.
Re: Studying Philosophy