Your rule of thumb should be this:
If it still impacts your life today - a felony conviction, a sexually transmitted disease, a history of cheating, or 42 children by 82 different women - then the person you’re dating needs to know about it pretty soon. They have the right to make a decision based on whether or not this is something they want to deal with.
Now, if you were smoking some dope and drinking on the weekends back in college and have no current drug or alcohol issues, then there’s no story to tell, other than you were an idiot in college. The information you need to provide should have a direct bearing on your life today (and therefore, the other person’s life as well by virtue of him or her being in a relationship with you).
If you do choose to reveal something minor about your past, you have got to do it slowly and not reveal too much too soon. The other person may not know you well enough to put it into context. Also, be prepared to reciprocate. You’re not the only one with stuff. Every human being has stuff. If they match your revelation with one of theirs, make it an opportunity to give the very thing you hope to get, which is kindness, compassion, and understanding. That doesn’t mean you have to date them or that they have to date you. The information might be a deal-breaker.
Finally, if you lay a bomb on somebody, you’d better give them the time they need to digest it. If they decide it’s not something they want to deal with, then you have to respect that.
Credit: Dr Laura.com