I just have to wonder, why would anyone here be too concerned with conventional wisdom, be it earrings or other things, when we all are being quite un-conventional in most other things?
One earring on a guy used to mean he was gay, (or queer if you lived in Texas, or a fag if you lived in Kansas). It also used to matter which ear you wore the single earring in. Does that mean that a guy who only wore one, but in the wrong ear, wasn't quite sure what he was?
My wife pierced mine about 15 years ago. Got a few looks, but, hey, they do come in pairs, so why not? If the thought embarrasses you, just get some inconspicuous little silver or gold ball stud types. And wear them ALL the time in public!! You'll quickly become less self-conscious. Then you can switch them out for your "girly" fun times. Believe me, the first time you wear some long danglies, it will be a wonderful feeling. Almost erotic!!

Myself, I wouldn't be caught with anything less than 3" long. My personal favorite is a pair of ruby and silver ones that are long enough to tickle my shoulders, and have a matching necklace. (Thank you Sweetie).
Like a lot of things, and the girls already know this, earrings are an expression of oneself, your mood, as well as the clothing you happen to have on at the time. They're not a one-kind-fits-all-occasions kind of thing. The good thing is, though, that once you have them pierced, you'll be looking for more pairs. and, yes, that's another thing I have too many of. Strangely, my wife has gotten me a few real gold pairs, but I hardly wear them, except for the 3" hoops. I kinda worry that I'll break or lose one. So far, though, I've only damaged one, in bed. A whole other story.
get 'em pierced. Both of them. You'll never look back, and as with so many other things, you'll wonder why you didn't do it sooner. What does it mean when a guy has both ears pierced? Does it really matter? That seems to be one hang-up that none of here should have.