Imagine, for a moment, that Chris Harrison is the patron saint of dating, and the gospel of The Bachelor is the single gal’s love bible. It stands to reason, then, that the first commandment of courting would surely be: “Tell thy date thy deepest, darkest secret as soon as thou cannest.” (Chilling, right?) While pouring your heart out on a first date is kind of a ratings necessity of reality TV, the same practice rarely yields a rose in real life. In fact, beyond the discomfort you’ll likely feel after revealing that you, say, have $200,000 in student loan debt or were a child star in Canada, it’s a promising way to scare away a potential love interest. Yet, the opposite end of the spectrum can also be problematic: You certainly don’t want to wait until you’ve been married for a decade to disclose that you have a long-lost twin sister living in Albuquerque.

So when is the right time to bring up important info that isn’t quite first-date material? And how do you do it in a way that causes the least amount of stress to your relationship? Well it’s complicated since there’s no hard-and-fast deadline for spilling your soul to your S.O. Just because you’ve been dating six months, or a year, or even two years doesn’t automatically mean you’re ready to share (or that they’re ready to listen). Trust, says relationship expert Terri Orbuch, PhD, author of Finding Love Again: 6 Simple Steps to a New and Happy Relationship,” should be your guiding principle.

“The best marker for when to tell a significant other a sensitive piece of information about you is when you trust the other person,” she says. “You trust someone when you feel that they won’t hurt or deceive you, that they have your best interests at heart, and they are open and honest with you. Trust takes time to develop in a relationship.”

“The best marker for when to tell a significant other a sensitive piece of information about you is when you trust the other person.” —relationship expert Terri Orbuch, PhD

Jaime Bronstein, relationship psychotherapist, agrees that there’s no use in designating a timetable for feeling comfortable to open up. “It could be two weeks, it could be two months,” she says. “It really depends, because all relationships are different. Use your intuition—it’s your biggest tool. Ask yourself, ‘Do I feel like this relationship is solid enough yet for me to disclose some information?’ Wait for that deep connection.”

And while it’s important to only open up once you feel comfortable, waiting too long causes its own problems. “If you had murdered somebody and you’re about to get married and you disclose that to your fiancé—not a good idea,” Bronstein says with a laugh. When what you’re disclosing brings your character into question, if you knowingly wait too long—like say until you live together or are making long-term plans—to share, you’re just being manipulative and compromising the authenticity of your relationship. The same goes for details that could negatively affect your partner’s future upon merging their life with yours—for instance, a sexually transmitted disease diagnosis or a significant amount of debt. So, if you sense that if you’re on the cusp of a serious commitment, like an engagement, Bronstein says it’s best to have Kondo-ed your skeleton closet.

When what your disclosing brings your character into question, if you knowingly wait too long to share, you’re just being manipulative and compromising the authenticity of your relationship.

So now that you’ve got the timing thing nailed how, exactly, do you go about dropping your news? One thing you shouldn’t do: Lead in with the dreaded “We need to talk…”

“Don’t make it a big deal,” says Bronstein. “If you have a casual attitude about something, then they naturally will too.” Of course, not every conversation will go as planned, and there’s a chance your secret won’t go over well with your partner. Bottom line, says Bronstein, if they can’t take it, they’re probably not the best fit for you.

There’s someone who will accept you—so long as you let them in on the details when you’re ready—for who you are. Then you’ll geteth that final rose.

With conversation covered, here’s the case for always wearing sneakers on a first date. Plus, first-date outfits that would spark joy in Marie Kondo.