I recently ordered a pair of 2g silicone earskins with 1/4" wearable area.  They popped in perfectly in my right lobe, but for some reason will NOT fit right in my left lobe.  Do you think I should order one 1/4" and one 5/16"?  

 This is what happens with my left lobe.  I fold the earskin in half, and then half again and put it in my hole.  It pops open, but the there is one place where it will not lay flush with my skin so it pokes out.  VERY FRUSTRATING because I love the way they look in my ears. 

I guess I just wondered if it's normal to have to order different sizes... 

There's a crappy pic, but you get the idea. 

My left lobe is thinner than the right, buying one of each size would probably be more comfortable for me too.

 I misunderstood what you typed, I thought you meant the wearable area!

you mean it like sticks out on the edges? if its that id say buy one in a bigger wearable area

if theres just a little section that like, dosent open properly, sometimes your hole might just not be big enough to accomodate them yet, that happened to a friend of mine, it went away after a few hours of wearing, and permanently after he stretched up a size temporarily 

EDIT 

oh crap! i didnt see that you posted that pic it didnt load on my comp, yeah that same thing happened to my friend and we just found out it was becuase his hole wasnt big enough, maybe tape up a little for a day or so then try again. 

Mine do that until I fiddle with it a bit and just straighten the back and it usually pops into place. I also suggest just waiting a bit to maybe let them loosen up if you haven't been at 2g for a while. 

 Even at 1/2" mine do that and simply need to be smoothed out.. They will in fact pop into full shape.  Try using a q-tip to push it flat.  They do need a bit of 'fiddlin' around with.

 IMO.. it just means that one of your ears is stretched out a little more than the other. if your other one fits fine and looks good then you don't  need to buy another one. Just fiddle with it more and get it to open up. If it still won't open then you might need to stretch just a teensie bit more with tape until you can fit the earskin properly.

Trust Amanda... she's the earskin girl, hehe! :) 

Thanks for all your suggestions guys!  I will keep messing with it! 

The first time I put my 2g earskins in they did the same thing.

My ears just weren't perfectly ready for the very thin silicone, I waited a couple more days, and then they opened up properly. It was another couple days before I could wear them to sleep, because they'd keep folding in when I put any pressure on my ears.

Not sure how long you have been at 2g, but maybe your ears just need to heal a little longer. OR, maybe you need to stretch up a little bit with tape, as suggested already. 

I've been at 2g for about a week...My left ear does seem to be healing a little slower than the right, so I'll give it some more time and try again in a few days.  Thanks! 

I had to wait about 3 weeks (was over 2 the first time I tried) before they wouldn't fold in like that, I think you're jumping the gun a little. Give them another week at least.