I'd attempted to read it 2 or 3 different times in the past, but it never made sense to me. Seemed too mystical and out there.
I gave it another attempt recently, and this time I got a little more serious -- I looked at a bunch of different translations.
It turns out, there's some immense differences in how people relate to and translate the work. I looked around, and I found these three versions free online that work really well together --
http://www.beatrice.com/TAO.pdf
http://www.bu.edu/religion/files/pdf/Tao_Teh_Ching_Translations.pdf
http://www.integralbook.com/wp-content/uploads/2012/03/Tao-Te-Ching.pdf
The first is written in very plain modern English with slang. There's some disjointed parts, but overall it's good at getting the basic message across.
The second has side-by-side versions of many different translations/interpretations. There's around 8 different translations of each chapter.
The third abandons the prose-like format and attempts to flesh out a long and lengthy explanation without assuming any background knowledge of the premises the Chinese copy might have had.
They work really well together. It's a short work, you could it read it in an hour or two. For interesting passages, look them up and go deeply. Highly recommended.