I don't know what to think of this boy (Please read, kind of long but I have NO idea what to do at all)?

[Repulsia]

He sounds like he's keen but is not confident, is very nervous and not sure how to conduct himself. I think he rambles when he's nervous.

Think about him for a minute, what do you like about him, what do you not like about him?

I'll break down how I would interpret what he said for you;
He kept mumbling to himself, half speaking to me, half speaking to himself and was saying stuff like "If I'm a good guy then I get friend zoned.." - This says to me that he's nervous and wants to be validated. He's desperate to know if you like him, if he's in the friend-zone or not. Obviously he's rushing things but he's anxious.
"I hate seeing couples, it makes me cringe." - He's looking for you to agree with him. Either by criticising a couple or by joining the enemy and becoming a couple.
He kept asking me stuff such as "Where do you want to go? It's completely up to you." - His indecisiveness is really him testing the waters, letting you take the lead because he doesn't know what to do and doesn't want to pick something you wouldn't enjoy.
"I told my brother I was easy earlier today and he laughed at me, well, I am easy.." - I bet that conversation with his brother never happened, he's trying to flirt and drop hints but isn't very good at it.
"I don't understand how couples get around to having sex, I wouldn't know how without it being awkward." - aww that's a fair statement and kinda cute. He probably wants you to initiate or tell him how you think a sexual encounter begins.
"Come here then." and hugged me - He got brave, good on him!
he picked Tuesday - because Tuesday is sooner than Thursday!

I think yes, he does like you but expressing it is not his strong point. How about you, do you like him? Thanks for posting a question that's well expressed and not complete nonsense like most teens on here!