How hard is it to ask "What's Wrong"

It finally happened. We started talking about living together. It only took me getting upset and crying over the smallest things for him to finally ask "what's wrong". We had just finished watching Garden State, I bought it the other day and brought it over to his house to watch it on the weekend. The first time i saw it, i loved it. It made me laugh, it made me cry, it made me think.. what more could you want? Well, he hated it. Ok, he didn't say he hated it, but when asked what he thought he replied "meh.", which i took as he thought it was a big piece of crap... And because I've been a bit stressed with the whole not talking about living together thing, it made me upset that he didn't like it. Stupid, huh? sometimes i get upset over the stupid things, but i'm a girl, it happens. Anyway, i started thinking about how i always make him watch movies that he ends up hating, drag him to places that he has a boring time at, and it just seems like i'm always making him do things he hates. What do i do in return? That day it seemed like I don't do anything in return (later realized that i do..and do lots). So I got more upset and went and just laid on his bed in the dark... he fell asleep on the couch, and i just laid crying in his bed. Eventually he got up and saw me laying there and asked what i was doing. I said "laying". so he turned the tv off in the living room and came and laid beside me. I think he was about to fall asleep again, then I started crying a bit and he noticed (finally!). So he asked "what's wrong". I said something like "sometimes I feel like a really crappy girlfriend", he asked why, i told him what I said previously, and he laughed. Just a note to guys - DONT LAUGH AT YOUR GIRLFRIEND WHEN THEY'RE UPSET AND CRYING! Even if he did think i was being ridiculous, he shouldn't have laughed. Then I told him that I don't know if I'm making him happy because he never tells me i am. He didn't say anything. there was a long pause... then i said "Do i make you happy?"...there was another pause and i started crying again because a pause after a question like that can never be good, right? Then he said "mostly". And there it was. When I asked him "when dont i make you happy?" he said when he asks me things about when we have kids, i say "i'm not having kids for years..." so i told him that i say that because i want to talk about LIVING TOGETHER...
I came to the conclusion that i think of things in the order that they come, he thinks of things ahead of time. I'm all, we should talk about the next step, and THEN talk about marraige and THEN talk about kids. But he thinks we should talk about marraige and kids and THEN talk about living together.
Apparently he tried talking about living together a while ago and i said we weren't ready.. and he was waiting for me to be ready... i don't recall that happening.
Anyway, we started talking about financial stuff, what we could afford, our options, etc. We're still not sure what we'll do, it's mostly me that needs to figure stuff out since i've never lived on my own, never paid rent, never really budgeted, nothin'! But i do have a bunch of money saved up now, almost enough for say, first & last! Once i start my new job, i should be able to save tonnes of money. The thing is, he's really in dept with school loans, car loans, credit cards, etc. So in theory, i do have more money than him. I only have a $500 limit credit card which i usually pay off right away, i have my car loan which isn't nearly as expensive as his, and my car insurance. I haven't had any problems paying them off, and with my new job, i'll be making like twice as much (if not more) than i was at my old job, i really think i'll be fine. I can always pick up extra work during slow months.
I've tried to work out roughly how much i can afford, but it's hard since i dont know how much say, a phone line costs, or cable, or hydro or anything really.. like i said, i dont know any of that. It's something we'll have to work out together.

Well, i've written a lot here, i think it's time to stop.. not like anyone reads my journal anyhow.