I hope you do someday, cosplay is really awesome! Almost as awesome as Lulu. Actually, it MIGHT be a tie. No, really.
Though I haven't had issues with self esteem, cosplay has made me a significantly happier person. (Sorry for reading some of this conversation... ^^,) And you meet all kinds of cool, nice people at conventions, and, and... Stuff. x3 I've cosplayed outside of conventions too, with small groups of friends at prop parties and stuff too... It's just such a fuzzy feeling in your chest.
You have no idea how shy I am! I barely go to classes at college because I can't stand being surrounded by strangers... But when I'm cosplaying it's like I'm a different person and I kind of forget I'm shy haha You should try it someday, it's really fun and it helped me a lot to overcome my shyness ^w^
Actually I think cosplaying helps a lot with gaining confidence. I've never felt so good about myself before I started making costumes and taking pictures. Every "omg you look so cute on that cosplay" makes me feel SO good, you have no idea haha I never get any kind of compliments in my life outside cosplay, so I really really appreciate when I get comments on my costumes ^w^ And Lulu is a great choice for a first cosplay, the costume itself isn't that complicated :3 I really hope you decide to give it a try someday!