For my first ever cosplay I did Hatsune Miku - the magnet version and my friend was Luka.
when I went off to the con I said "Well I'm off to be a robot lesbian with katie(my friend)" and my mom just said "have fun, take pictures". Needless to say my mother is pretty cool with cosplay (she's a seamstress and likes to help me make costumes)
I still can't believe I actually finished a cosplay.
Tentative Cosplay List:
Porrim Maryam - Homestuck
Kirino Kousaka - Oreimo