You're stupid, so why do I still like you???

So theres this boy that I didnt know at the begining of the year but I got to know him and actually got to like him. I looked at him as a really good friend then as something more. I'd never really had much experiance with boys so when he started flirting with me i thought he liked me. So when my friends would ask when he turned his back "Does he like you?" I'd always say yes.

Now that it been a few months im ready to tell him that i like him too, but ironicly that same day he was just talking and he says, "You know i used to like you." and i'm thinking WTf? used to......???? so i never told him i liked him... Should I have????

We were akward for awhile then he dated some one else and i got over it, but they broke up and recently he's gone back to flirting with me again.... he always wants to talk to me and txts me every night... I just dont understand does he like me or not?

Then my friend takes my phone on the bus one day and texts my other closest guy friend, with out me knowing, "Do you want to go out." He walks up to me the next day and says "Sorry i didnt get to answer your text last night." and i said "What text?" my friend pops in saying "The one i sent asking him out for you." i open my big mouth and say "oh i didnt say that or mean that..." he takes it the wrong way and gets offended and walks off saying "The answer would have been yes if that wasn't a joke."

and now im sad cause i dont know what to do about either situation.... Help me please lovely people!!!!!!