I am currently dating a wonderful and very understanding guy, the kind anyone would be downright lucky to have. But previously, I've had a spate of bad relationships which have left me slightly insecure and hurt. Moreover, I find myself unable to say no to a lot of things like going out (when my policy is to save up money for all the things I plan to buy later), eating out (when I do not), missing classes (losing out on hours that could have been spent writing or studying- I am an undergrad)... We're dating without any clauses, but we're close nevertheless. We have had wonderful times together, but it all leaves me guilty towards the end of it. I am the sort of person who likes to utilise all her time into constructive things.
Plus, I messed up my high school exams because of dating. I see college as my last shot. Plus my mother has expectations of me that I must fulfil no matter what. I love her.
What do I do? Am I being way too obsessed with the whole thing? Should I take it easy? Or do I focus on my career? (I some good friends, and I'm happy with them. Losing him... I don't know. While I know he will understand, I may lose him.)
HELP!

I may be reading you wrong, but it sounds like you have an 'all or nothing' approach. You can't say no? Have you tried talking about your school schedule and your finances with him? Not at the moment he asks you to go to a restaurant, but sometime when you have plenty of time to present your thoughts carefully. If you live in fear that he might leave you without ever approaching the two subjects, you might never know that he will be perfectly understanding and happy to compromise.
In fact, the inability to say no, to voice your wishes and opinions, might be at the crux of many a bad relationship in the past. Resentment builds up over time without even realizing it, I think. I know I have done that, and many of us have, especially when we are eager to please at the beginning of a romance.

I cannot get myself to say no.
He doesn't know my school schedule but is particular about me not missing out on classes.
As for the paying bit, I admit I feel embarrassed when I'm not in a position to pay for myself. Nevertheless, he drives me around helping me get a lot of work done; transport around here is either time consuming or expensive.. He has opened up to me about his feelings, his fears. I find myself unable to, sometimes, despite knowing he has been there for me and has supported me through the worst times here.
I'm finding it difficult to handle it all in one go.

So he has 'opened up' to you, but you haven't to him - why, because you are afraid of losing his car to drive you around, buying an occasional meal when you don't have enough, supporting you through the worst times?
Not good for either of you. He sounds nice enough to adjust to your school needs if you just say so, but you are the only one who can make the choice between going along with his desires to go out and ruin the study time, vs. telling him you need more time for school and thereby risking losing what he has to offer. Personally I would tell him. How you tell him is key - I'd make a list of your month ahead and map out exams, papers due, etc, and put free time on a calendar, and make a copy for each of you. Sounds too practical? Not so. It's to save the relationship and your future career.

So he has 'opened up' to you, but you haven't to him - why, because you are afraid of losing his car to drive you around, buying an occasional meal when you don't have enough, supporting you through the worst times?
Not good for either of you. He sounds nice enough to adjust to your school needs if you just say so, but you are the only one who can make the choice between going along with his desires to go out and ruin the study time, vs. telling him you need more time for school and thereby risking losing what he has to offer. Personally I would tell him. How you tell him is key - I'd make a list of your month ahead and map out exams, papers due, etc, and put free time on a calendar, and make a copy for each of you. Sounds too practical? Not so. It's to save the relationship and your future career.

I have problems opening up to anyone who isn't my mother or best friend. I have been deserted and bullied long enough for me to not trust most people with what I feel.
It gets awkward as hell and I'm trying to overcome past feelings.
I have a meal plan at the dorm, so I will not die of hunger if I do not have enough to go out and eat. If I ask my father too, he will send some more capital over, except I happen to have spent quite some on travelling and competitions I participate in, so out of a sense of responsibility towards how I spend, I refuse to spend much on other things that can wait, going out and eating out included.
That my college fees is obnoxiously high does not make me feel any better; I see my father working hard every day. I can never get myself to justify spending all that much simply because it is my father's hard-earned money, not mine.

You are doing a good job of talking (to us) all around this particular boyfriend.
I know it isn't easy to wonder if you will be treated the same by this man as you were by past men, or if there is something in you that sets yourself up for disappointment because you expect it now. It's easy for all of us online to say that you need to be more open! We aren't there.

But I think you need to be. You expressed the problem pretty well here, and yet can't tell him. And when I offered a practical, concrete start (the calendar), you didn't address that at all.

You are doing a good job of talking (to us) all around this particular boyfriend.
I know it isn't easy to wonder if you will be treated the same by this man as you were by past men, or if there is something in you that sets yourself up for disappointment because you expect it now. It's easy for all of us online to say that you need to be more open! We aren't there.

But I think you need to be. You expressed the problem pretty well here, and yet can't tell him. And when I offered a practical, concrete start (the calendar), you didn't address that at all.

I'm sorry. I believe my second comment did not get posted. I'll say it again, never mind.
That is a pretty neat idea. I'm actually working on it. Thank you :)

:)