How to break deal breakers with matches?

Rather, I see it as my own responsibility to be aware of what my dealbreakers are and to look for them/ask about them accordingly. I'd also almost argue that for many things you get a better sense through observing someone's behavior than talking about it.

It's definitely tricky. No I wouldn't personally ask someone about their mental illness. I don't know your ex but if he did disclose something early on do you think he would have admitted to being non-compliant? I'm just curious whether disclosing he had it at all would be enough to send you for the door? It's also hard because every mental illness is different and there are quite the continuum. Just hearing a label, doesn't, for me give greatest indication of the impact it would have on a relationship.

Wiseman, I'd rather talk about the theory as opposed to my actual life. I got a good sense of what everyone thought about my life/chances already, so I'm looking more for how other people got across difficult personal issues.

I feel like mine is an easier fix, because if I can get hired somewhere with a decent enough salary, my situation will change dramatically and quickly, whereas mental/physical/addiction type issues I think would be far more difficult fixes. "find a better paying job" I think is more appealing then "become undepressed or unaddicted to drugs and not pay out child support" or something...

As far as grad school goes, the going into more debt aspect has been unappetizing, as has the fact that I generally have worked a really varied schedule (and if I changed my availability, I'd have less hours/been more broke) - I keep trying for some 9-5 type jobs where I can commit to a night time school schedule. Its easy for armchair quarterbacks to say "go to grad school" except if you work 9-5 or 2-10 or 4-12 pretty much at random its not so easy.

Also as I've said a number of times, regardless of % paid towards rent and other things, I didn't have extra money to put into something a graduate degree, it would have been all loans (which I've considered). I spent all my money on living expenses/gas/car insurance/undergrad loans.

Okay,

My previous attempt at this got a little too personal, I'm going to broaden this question... There are obviously some things that are true about everyone that they don't want anywhere near their profiles... You want the best "version" of yourself out there for everyone to see... So how/when do you disclose the "other parts?"

I came up with 3 different sorts of scenarios...

1) You got divorced/ended a 5+ year serious relationship within the past year and are still emotionally sensitive but want to get a fresh start(emotional issue)
Unless asked about your relationship history there is no need to bring this up at all. If you are not emotionally ready to be dating, for whatever reason, that is going to show up very early on.

2) You have some combination of embarrassing health issues... I had a co-worker that I worked with for a while that had bad hips, Crohns, and awful seasonal allergies (and she couldn't take all the medications at the same time so the least evil was to have horrible hay fever for the spring/summer and sneeze 70+ times a day) (so that's a purely physical issue)
If you have any physical problems that prevent you from living a normal ordinary life then this should be divulged early, possibly even before the first date. When it needs to be divulged is proportional to the severity of the disability. Bad hips could be something that prevents you from climbing a ladder yet has very little impact to your daily activity level to you have to park in a disabled spot and ride around in a scooter chair and you are long overdue for surgery. Allergies could be that you are affected if you go outside to you are allergic to pets of certain types.

3. You have bipolar depression that's fairly under control but still flares up when you get really stressed out so you know you can get amazingly moody (to put it nicely) (which would be a physical and emotional issue)
I am going to expand this some and it is in many ways related to number 2. If you have an illness that is controlled by medicine, be it mental or something like blood pressure, this should be brought up somewhat early on. Many times certain mental problems can be well controlled through medication and the person can lead a very normal life. However, oft times these people have a tendency to quit taking their medication and can become downright dangerous. If the medication is for a physical problem not taking it could be deadly.

So those things wouldn't go on an eHarmony profile (this is all purely hypothetical, I'm not asking for personal advice) but how/when would you break this to a match?
The bottom line is that the severity of the problem determines when it should be revealed.