Preemptive Planning

In a bout of mega drama earlier this week, I cried to my mother that my life would never get started and I would spend forever waiting and waiting for things to happen to me that never will.  I won't lie, it is a topic of severe and pervasive frustration for me.  I have been in school (well, higher education) for seven years now, which has prevented me from getting a job, getting married, getting a dog, buying a house, or generally doing anything of any consequence.  It is frustrating, at 24 going very very quickly on 25, to be no better off than I was when I was 18 and first starting college.  In fact, sometimes I feel like I am worse off--I certainly have less money and there's an awful lot more debt.  I am, however, prone to dramatization and high levels of stress (corresponding, no doubt, to my impending graduation, joblessness and the necessity of an intense bar prep schedule coming quickly upon me--which, in my defense, makes it a little more understandable) frequently make me have hysterical crying fits.  My mother, though, for all her good qualities, does not indulge my self-deprecating fits and takes a much more pragmatic approach.  You're fine, she says.  You're in law school, which is better than most people.  Pssh.  I tried to explain to her that law school is one of those things that SOUNDS really cool to people on the outside looking in but that, in real life, it sucks and all law students are incredibly miserable.  She doesn't buy it.  Well, she isn't living it.
I also made the mistake of telling Andy that having a puppy was the only thing I could control and the only thing I had to look forward to for sure.  What I meant was...I can adopt a puppy no matter what happens.  If I don't graduate, I can get a puppy.  If I fail the bar, I can get a puppy.  If I can't control Andy's spending/saving habits and we don't get engaged, I can get a puppy.  I am really uncomfortable that so much of my life hangs on so many other things that I can't control.  Andy said that our upcoming engagement was much more exciting than a puppy and that I should concentrate on that.  He went on to say that we would more than likely be getting married before I got my first job.  Well, that does sound good.  And it made me feel a little better.  If I were completely honest with myself, I would expect to pass the bar and find out about it sometime in late October, look for a job and interview (if I don't have a job before then), and land a job somewhere between November and January.  A wedding before then?  Hmm.
Am I jumping to conclusions by assuming that means that Andy is planning on proposing in a few months?  I told him that I wanted to get married in August or September originally and that, in order to plan for that, I needed to be engaged by March.  I had kind of gone on the assumption that we were not really going to get engaged or married that quickly (because I know that there is no longer any money in Andy's savings account) and had stopped anticipating my imminent wedding.  But now Andy's words have sort of made me start to wonder anew whether or not preemptive planning is a good idea.  Of course,  I would be lying if I said I didn't have some sort of idea (or, you know, an entire wedding powerpoint full of general plans) about what I want to do...but I had more or less stopped actively planning.  Does this mean that I should go on Andy's word, and plan in the hope that the engagement is forthcoming, or should I just wait and be coolly optimistic but not overly excited about a relatively vague "promise" of an engagement?  It's a difficult question.  I generally am of the opinion that to be proactive is best, but where it comes to weddings, I am a little bit too emotionally invested.  I am feeling cautious but optimistic.  I WANT to take it and run with it...but, then again, that may be a very, very bad idea. 
He keeps saying things like that, which at least means that he is serious about getting married--and relatively soon.  But relatively soon can mean a lot of things.  In fact, I would generally say that "relatively soon" in wedding-talk probably does NOT mean this summer--but I could be convinced that to be married relatively soon would mean the following summer.  But I don't think that's what Andy is thinking, because he keeps saying things like after the bar but before my job, etc.  Let's face it--Andy is a boy, and boys know nothing about how long and involved the wedding planning process is. 
...So should I plan, or is it a recipe for disaster?  I have to admit, just him saying that makes me feel much less close to another hysterical crying fit.  But I do still want a puppy.