You've met a sweet, wonderful woman and you want to get to know her on a deeper level, but there's a lurking cloud of gloom from your past threatening to rain on the new happiness you're just starting to build. You want to tell her about it, but it's something you're ashamed of – something serious, like cheating on your last girlfriend, a large amount of debt or maybe even a former addiction! How, and when, do you tell your girlfriend about the huge, dark secret in your past?
Is Your Secret Old and Irrelevant, or Impacting You Currently?
Before you start to sweat in your shoes, think about how much real-world effect your past transgression could actually have on your new relationship. There are all types of secrets — everything from a nasty divorce to theft — and for sure, many of them might cause your girl to hesitate. But stealing money from your parents when you were 17 isn't going to weigh upon your new relationship in the same way as would, say, a large unpaid debt that you're still suffering from now. There's a big difference between a trust issue from the past and an ongoing issue that could prevent you from having a child or owning a home with your partner in the years to come.
Are You Confessing Just to Make Yourself Feel Better? If your dark secret is only a slight misstep that you rectified long ago, something that will have no impact on dating or your life now, first consider whether you need to share it at all. Are you telling your dark secret to help her and the relationship, or are you doing it to make yourself feel better? Remember, no one has the right to inspect every nook and cranny of your life, and not every woman wants you to take the skeletons out of your closet and shake them in her face. You can always make a confession to a priest, a psychologist or maybe your best buddy, but you don't necessarily need to tell all your past faults to your new lady friend. Do it because she needs to know, or because it's the right thing to do, not because you feel compelled to show her all your old dirty laundry.
How Do You Confess to Something that No Longer Affects You?
Let's say your dark secret was wrapped up a long time ago but it's something you need to tell. It's something like an addiction you had years ago, or a betrayal of your parents — something that potentially hurt your family and friends at the time but that you worked hard to move past. For this scenario, it's definitely not something that could hurt your new girlfriend in any way, but it is something that she needs to know if she's going to understand you. We recommend that you break it to her relatively early in the relationship. Don't spill the beans on the first date, but don't wait too long. Trust is the absolute foundation of a relationship, and waiting until you know each other a bit is fine. However, stalling past that point can have serious consequences as to whether you're perceived as a forthright person.
Here are some tips to help break the news without breaking up a good thing:
1. Wait until you're in a comfortable conversational situation, such as having dinner or having drinks before a movie, so she'll be at her most receptive and understanding. Or, if the conversation has turned serious and she's just revealed a dark secret of her own, you know she'll be in a good place to listen to yours.
2. Lead with a compliment about the relationship. "I've had such a great time getting to know you, I don't want to spoil it by keeping something from you."
3. Stress the secret's relative unimportance, and that it's ancient history.
4. Tell about the epiphany that led you away from your mistake.
5. Point out the deliberate, constructive things you did to change your behavior and move on.
6. Show the contrast of then versus now. Provide some kind of assurance that you are the kind of person who would not do this again because you're a different, wiser man.
How Do You Confess an Ongoing Secret, One that Could Affect Her?
If your dark secret is something that still affects you personally and could also affect your relationship, such as bad credit or a sexually transmitted disease, it could be harder to talk about than something you did years ago that's long past. But here the need to tell her is more urgent. So make your spin on this problem as constructive as possible. In addition to all the above tips, lay out the winning action plan you're currently taking to resolve the situation.
1. Stress why the behavior that got you into the situation is not behavior you would follow now. For example, if you got into a debt because you gambled your money away, tell her that you've attended Gamblers Anonymous or that you make it a rule never to watch a sporting event that you used to bet on.
2. List the steps you are taking, including a definitive timeline, to get yourself out of the situation as best you can. If it's debt, tell her you've consolidated your debt and are making payments. If it's an STD, tell her you've seen doctors and are undergoing treatment to cure the disease or minimize your symptoms so that they recur less often. Whatever it is, explain the timeline and how you are adhering to your responsibilities during that timeline.
3. Explain how she can keep dating you without worrying about getting saddled with your problem. One of the most basic concerns that accompany a new relationship is a fear that your new partner is harboring a problem that is going to become YOUR problem. You've got to address this concern.
What If It Wasn't Your Fault?
Some ongoing dark secrets can affect your relationship but are not so much mistakes on your part as calamities that happened to you despite your best planning — like telemarketers and taxes, they couldn't be avoided. For example, you may have credit card woes due to an illness that you were not insured for. Or you may have contracted an STD (or a large debt) from a previous wife who cheated on you and brought home an unsuspected surprise. Unfortunately, blaming your dark secret on an ex-wife doesn't change the facts for your new partner. Your lack of "guilt" doesn't mean you can shrug off the gravity of your situation. You still need to come clean and take responsibility for the situation (even if, in your heart of hearts, you feel most of the responsibility lies with other people, or just bad luck). Remember, the outcome is the same as if you'd made the mistake yourself, and the potential risks to her are still real. If you're frank and open and answer any questions she has, hopefully she'll respect the fact that you're being honest and acting responsibly. Your refusal to play the blame game will show her that every day you bravely tackle a problem you never asked for, and do it without shame. And there's something noble in that.
Be Prepared for Rejection, Be Prepared for Understanding, and Good Luck
Whether you're dealing with an old misdemeanor or a recent trial, sharing a dark secret with a woman you're starting to date can be daunting. And truth be told, not every woman will respond positively, and you can be sure that no two women will respond in the same way, but when you stand up and treat the situation with respect and honesty you'll have the peace of mind that comes with doing the best you can in a difficult situation