I found this article interesting. When is the best time to “tell on yourself.” When you start dating someone when do you tell them some possibly unpleasant details about yourself? Feel free to make any confessions here too. 
Not really a problem for me at the moment. My SO knows everything about me and me her. I just read the article and was wondering what the right answer is. I have not made up my mind yet. I’m leaning towards better sooner than latter.
There are three factors here that immediately come to mind:
The other person’s “need to know.” If they’re going to be cooking for you and you have diabetes, you need to tell them that before they go shopping. If you spent a little time in jail twenty years ago for joyriding, you can probably wait a bit longer.
The degree to which not knowing will hurt the other person emotionally. If I have two children from a previous marriage, that’s something she should probably know pretty quickly. If I had a devastatingly bad relationship years ago that doesn’t really affect me in any way, that can wait.
How bad the unpleasant detail is. If you have a manslaughter conviction, you should probably come clean in the first few dates. If you exchanged a few punches with a priest on St. Patrick’s Day in 1998, that can wait.
Being asked directly kind of trumps everything. I don’t often volunteer that I’m divorced, but I’m not going to lie or Stonewall if asked. Funny story: I also don’t volunteer that I’ve done academic work on vampires, but I used to keep my vampire books in the bedroom for space purposes. After a few dates with a young woman a few years ago, we ended up back at my place to make love. Seeing this big ol’ shelf of vamp books didn’t put a damper on things, but she admitted later that she thought twice at that moment.
Please tell me that isn’t just a random example!
Some things you take to the grave. For the rest, I think when the consequences of telling are low and/or will have little negative impact. Beyond the deep dark, there’s no time like the present.
So the guy has impotency issues and a CPAP? And she thinks he should have waited until… when to tell her? I’m not old enough to worry too much about a sexual partner’s ability to perform but if that were a concern, I certainly would want to know about it very early on. It’s totally relevant!
Potential deal-breaker issues (and you know your issues, you know which ones those are) should be addressed prior to sex, certainly, and probably within the first couple dates. Why drag it out and get to a point where feelings are involved, you know?
It’s not like I KNEW he was a priest or anything.
On our third date, my wife told me several very significant facts about her past that she felt I should know. The specifics are not important for this discusion, but they were the kinds of things that might have given some people pause. It was very brave of her to do it as early as she did, but she didn’t want things to go too far before telling me.
Far from turning me off, the honesty, courage, and trust in me she showed vastly increased the respect I had for her, and probably made it easier for me to fall in love with her. The fourth anniversary of our first date is two months from today.
Oh, well that’s all right then… 
Seriously though, that is a fun thing to be able to tell people, assuming neither of you were seriously hurt!
Wife & I know each others black places.
Works for us.
During
I am (quite genuinely) curious about what sort of confessions fall into this category, and why.
Shortly after the statute of limitations expires…
It really depends on what you’re disclosing. Serious health issues? Within the first few dates/pre-sex. But there is never really a good time to complain to your new or potential SO about how much you hate your bitch ex and that you don’t trust women… neither should anyone brag about their sexual skills. Show, don’t tell.
I myself have nothing to hide except a history of depression/anxiety, and currently bad credit I’m working on rebuilding. Those are things I’d bring up within the first few months of seeing someone new, but certainly not right away (as I consider them my business, something which will impact another person very little unless we end up very serious).
I will say that my current romance began on pretty shaky ground, with both of us going through depression, still carrying a lot of baggage from serious break-ups, in the process of changing our lives hugely, and unwilling to commit/attach to each other. There was a lot of confessing and oversharing early on. And it worked for us - we both knew the worst of the other right away, were still interested, and now we’re both in healthier places a year and a half on, thanks in part to being together. But I think it helped that we had known each other as mostly-casual friends for years before dating.
I forgot to mention that I had known my wife-to-be in college, 30 years before we reconnected. And I agree, it made things a lot easier for us. I hadn’t known her well enough then to have a glimmer about her issues, but we were both more comfortable with each other than we would have been with a completely new person.
And I imagine that our long previous acquaintance made it easier for her to trust me and open up as she did.