(The Root) —
"I have a major secret that I've been keeping from a woman I'm dating. I'm afraid if I tell her too soon, it will scare her away. And if I tell her too late, she will think I am not trustworthy, and she will leave. When do you think is the best time to tell someone serious information?" —G.U.
Just like when you learn a new phrase and suddenly everyone seems to be using it, something similar happens when you have a secret. Whatever it is you're hiding, it's almost inevitable that the subject will be a topic of conversation the first time you meet or go on a date with someone you want to know better. That's actually the best time to divulge a secret — as soon as it comes up. Just put it all out there and have no secrets.
This is an opportunity that nearly no one takes. And that's fine. Unless your big secret is something that would make you unavailable to date by most standards — you are married, engaged or in a relationship, or your divorce is not yet final — you're in the clear about not confessing very early on. Secrets, by nature, are kept because you don't want others, especially strangers, to know your personal business. And no one reasonable will fault you for not spilling to someone you don't yet know.
But if you're interested in being in a relationship and you believe the other person feels the same, it's time to fess up — before you have sex. If your confession is about an STD, if you slept with someone she knows or with someone of your same sex, she needs to know prior to lying down with you. You don't want to drop a bomb on her after she's emotionally invested — which, if she's having sex with you, is likely.
Waiting until the person you're dating is in deep to tell him or her a secret is a popular method for confessing, but it's also entirely selfish. It's only done with the hopes that the person cares about the confessor so much that he or she won't leave when the confessor says whatever it is that needs saying. When it works, the secret-keeper often avoids rejection, but the emotional toll it takes on the other person is unfair.
There's also the risk that your partner could deal with your secret, but not your deception. It will be a doubly horrible experience for you if you get up the nerve to confess whatever's been weighing on your mind and you are rejected for, of all things, your timing.
I'm guessing that your secret is pretty big — at least to you — since you've even been secretive about it in your query. Still, please fight the inclination to go the dramatic route and announce, "I have something to tell you!" and let your partner's mind run wild during the pregnant pause(s) until you confess.
And do yourself a favor by not making whatever your big secret is sound as if somebody just died. Just get her in a space where she's comfortable and say what needs saying as casually and calmly as possible. Don't go on the defensive if she has follow-up questions, and if she needs it, grant her the space to think about what she's just heard and get back to you with her thoughts. Pushing for acceptance, as much as you'd like to know where you stand, will likely push her away.
I know you're worried, but things might not turn out as badly as you fear. People have an uncanny way of not doing what other people expect them to do in these situations. A guy I know was once terrified to tell a woman he really liked that he had an incurable STI. He took her to the boardwalk on a sunny day (i.e., somewhere where she couldn't storm out and leave him) to tell her. She looked at him in shock and said, "Really? Me, too."
Demetria L. Lucas is a contributing editor to The Root, a life coach and the author of A Belle in Brooklyn: The Go-to Girl for Advice on Living Your Best Single Life. She answers your dating and relationship questions on The Root each week. Feel free to ask anything at firstname.lastname@example.org.