I find it weird how everyone in person tells me that I should date a lot, enjoy a ton of "young loves" and meet a lot of girls before I ever get married someday. Yet, knowing how desperate and socially awkward I am, I imagine that I will probably just end up marrying the first attractive Orthodox girl that comes into my life that doesn't leave me after a week.
The 'playing the field' thing is a crock if you ask me. I never dated many girls mainly because I was always painfully shy. I was told all the sorts of things it sounds like you were and all it did was make me feel like I'd never meet anyone - if I needed to date loads to find the right one I was stuffed. What actually happened is that I met my wife at age 19 but we were just friends. A few years later that friendship turned into something more and we were married when I was 25. We're still happily married (12th anniversary this year) and I couldn't imagine life without her. Of those people I know who did play the field, I'd say the results wouldn't seem to justify the original advice.
A lot of it depends on what you mean by "playing the field". A lot of people generally use this term to denote going on lots of dates and gathering a respectable number of notches on your bedpost. Others (like I believe JamesR was using) just use the term but are trying to say you should date a number of people. In some cases like yours you really don't need to. For others, if I were married to the first girl I really dated I'd probably have shot myself by now. In other cases, it's just a matter of necessity. Most of the women I have had dated always had two or three guys at a time so it really is in a man's best interest to have a couple lined up and never get to attached to any one of them.
Really, dating and marriage in this society is like playing Russian Roulette with half the chambers loaded instead of just one. If JamesR is indeed so shy that he'll marry the first Orthodox girl who doesn't turn him down there is a very real chance that he could end up like you with the hammer falling on an empty chamber and then reap a great reward. But with frivolous divorce, alimony and the 50% rate, he might very well land on a primer, figuratively and literally.
Best thing you can do is be careful.