When it comes to dating, if and when you should air your dirty laundry depends on the nature of your relationship. When you first start dating I don’t think you should tell too much too soon. It’s good to maintain an air of mystery about certain things until you can at least determine if the person you’re dating is going to be around long enough to deserve or need to know all of your personal business.
Your partner should earn your trust before you tell them anything you wouldn’t want them to tell someone else. The longer you date and the better you get to know each other, then you can start revealing things that most people may not know about you. But before you get start sharing, I caution you to make sure that the information is something your partner can handle. Many people like to ask how many sexual partners you’ve had, only to turn around and act mortified by your response or the throw the number back in your face to judge you later on.
However, when you get engaged or think you should marry someone, you and that person should be at the point where they have been getting to know you over time and they are comfortable with who you are today, not who you were yesterday. If you don’t feel comfortable sharing certain things about yourself that could be a sign that you and your future spouse may not be as close as you should be.
You cannot start a marriage with certain secrets hanging over your relationship. Things like your finances or your relationships with your family and friends are things you need to be open and honest about. When two people get married, they become one in many ways, including financially, so it isn’t fair or practical to think you can keep your debt a secret to someone who will walk down the aisle with you and literally become responsible for half of it that day!
The same thing goes for your relationships with others. You are going to have to come clean about who means what to you rather than try to lie about your relationships in order to have your cake and eat it too. You will have to make some financial and personal sacrifices in order to make a relationship work and if you aren’t ready to do that, then you are not ready for marriage. Once married, how you spend your money will change to incorporate your partner’s wants. Your relationships with others will have to change also as your spouse becomes a priority and others become second in importance.
Whatever is in your past, don’t let it discourage you from sharing it and being intimate with the person you think you want to spend the rest of your life with. If that person is the right one for you, they will love you despite a few skeletons (EVERYONE has some!).