Things to tell immediately

If there’s something about you that you think can affect any long-term prospects and that more than two people know, you may as well ’fess up on the first few dates — especially if you feel that it may blow things. You can try to create an environment that makes sense, but keeping that big of a secret from the get-go adds pressure and nervousness at a pressurized time. If you’d tell a same-sex potential friend, tell your date. If your date is cool about it, you’re relaxed. If not, at least you haven’t invested much already. Information that more than two people have isn’t a secret. If your date is likely to find out sooner to later, you may as well tell sooner rather than jeopardize the relationship once it progresses and the additional factor of trust is introduced (as in, “If you’d lie about this, what else haven’t you told me?”). Any long-term relationship is based on trust. If you can’t trust someone, you can’t love that someone, so don’t start off hiding important facts. The list of things you definitely must share includes most of the biggies in life. You should share this information by the third or fourth date. Any earlier is unnecessarily brutal; after all, if you really don’t fancy one another, why parade the skeletons from your closet? Any later is viewed as a breach of trust (plus, not having shared can get you in more trouble than any upset that telling may now create).

• Previous marriages: How many times you’ve been married, how long you were married, and how long you’ve been apart. But don’t go into too much detail. See the later section “Keeping Mum.” Notice that you should confess previous marriages, not whether you’re married or separated or in the process of divorce. The reason? If you are married or separated or in the process of a divorce, you have no business dating at all — not until one full year after the divorce is final. I’m not kidding here. If you fit into one of these three categories, you can hang out with friends, work out, paint your house, become a temporary workaholic, take courses, volunteer — but you can’t date.
  
• Previous convictions and parole violations: What crime you were convicted of and how long you were in prison. (I’m sorta kidding here, but stuff happens.)
• Previous bankruptcies: How long ago you filed for bankruptcy and why.
  
• Previous kids: How many, how old, whether they live with you, and if they don’t, how often you see them.
• Previous sex change operations: What can I say? When should you share this information? You don’t necessarily have to share it when you first lay eyes on one another, but before the end of the third date at latest. Confessions of any kind — even “I think you’re swell” — need to be seen and heard in context. The best rule for when to tell is when you’d want to know if you were the one about to hear what you have to say.