My first real question. God bless you.

Dear Stephanie,
How much information is too much information? In what circumstances should someone stick a cork in it? is it truly that horrible to be honest? Why are men specifically "grossed out" and put off by honesty? What is "playing hard to get" all about? Really...
Sincerely,
Just trying to keep it real

Dear Just trying to keep it real,
I'm going to act on a hunch here. My guess is that you've been told you aren't a catch at some point. I'm going to say that you may have been rejected recently after a big investment and are feeling like no one will ever love you again once they get to know "the real you". NOT TRUE.
I know that when I rush into spilling my guts I'm just feeling so nervous and vulnerable I cant help but thinking "Yeah this is all fun now, but let's just get on with the inevitable."

I do not reccomend this. It has yet to work.

We all have traits that are less than appealing and as you get older and are in relationship after relationship, you can go one of two ways: you can start to think of these habits as permanent parts of who you are, or you can realize that you can choose learn from break-ups and adjust what you truly think ought to be.

Aside from everything, this is a NEW relationship. A blank slate. Game over, start again.
How much information is too much information? That's up to you. For me, I try not to offer up something unless it's clear that someone is ready to hear it. That's not to say they get to set the speed at which you dive but it is to say you need to recognize and respect where the other person in the relationship (any relationship) is at. If, three months into dating him, he's yet to tell you anything more personal than his last name, he's probably not ever going to open up and you should just walk away. You don't need everyone to know you're deepest secrets. However, if we're talking a couple weeks and he reacted poorly to hearing the whole of your psychiatric history, let's not label him a block of ice just yet.

Let me let you in on a secret that I've learned: When you talk about any problem at all, 9 times out of 10 all a guy hears is "fix it".

Perhaps that will help you to know when to stick a cork in it.
Also, as awful as it sounds dating, early on, is like a job interview: you want to put your best foot forward because you want the position. Would you say to a boss right off the bat that you aren't good at x, y, z in the hopes that it will save surprises down the road? No. You would realize that in the past you didn't succeed at x. y. z but that was then and this is a new job and you've learned from then. So when your weak points come to the surface at this new job you'll most likely know what to do. And your boss will be none the wiser...So keep the lip zipped about your past failures. And who knows, maybe you will face them but surprise yourself as you rise to the challange graciously, rather than falling on your stupid face.

Keep in mind that you aren't new at this. You have experience. You aren't apt to make the same mistakes. So don't go holding on to them and announcing them to everyone that comes along. Let them decide what they think of you from their experiences with you.

As for being honest, it is the best policy. THE BEST. But just because you keep something to yourself, you aren't neccesarily being dishonest. Like I said, you might go blabbing about something that just isn't true of you anymore. I know I'm a completely different person if I just change my shoes.
If you're asked specifically about your past, then answer the questions. If he chooses to judge you for it, remind him that he asked and also what's done is done and that it (probably) didn't have anything to do with him. But, honestly...honestly...a confidant man doesn't care about your past. They just don't.

This is separate from "playing hard to get". That's just a game of cat and mouse that makes things spicey, if you like that sort of thing..

So, keep it real. But most importantly, keep it here and now...not then.