The Reveal: When Do You Tell Your Date … That Thing?

when to reveal secrets on a dateAt a bookstore cafe in Boston, a woman in the audience had a question for me, the evening’s designated dating guru. There was something she didn’t want the men she dated to know about her. How long should she hide it?

I sat on a high stool in front of the room, microphone in hand, blinking. My book, It’s Not You, isn’t a dating guide per say, but it’s about being single and it’s very personal, so I often find myself in advice-lady mode. It’s something I’m still getting used to.

“Something you don’t want them to know?” I said, stalling.

“I’m a vegan,” she said.

I must have looked confused, so she explained. She was also a conservative Christian. She didn’t want men getting the wrong impression when she ordered tofu and quinoa.

Isn’t it funny? Our own secrets are so deep and dark. Other people’s are adorable.

But regardless of whether the issue is a dietary restriction or a criminal record, the question of when to share delicate information looms large for many daters, says Daniel Jones, the editor of The New York Times Modern Love column.

During the ten years Jones has edited the column, he has read many submissions from people fretting about when to do “the reveal.” When do you tell the person you’re dating that you’re a recovering alcoholic or that you recently filed for bankruptcy? When is exactly the right time to mention you have a 2-year-old daughter who lives with her mother in another state?

“We all have failings and insecurities—physical and emotional scars, divorces, STDs, cancer—that we’re trying to hide or at least de-emphasize early in the relationship. I’ve heard from chemotherapy patients who have agonized over the ‘wig reveal’ and from someone with a disfiguring leg disease who agonized over her ‘pants reveal,’” Jones writes in his delightful and wise new book Love Illuminated: Exploring Life’s Most Mystifying Subject (with the Help of 50,000 Strangers).

He also heard from me. A few years ago, I submitted an essay about my sparse dating history, and the embarrassment I felt when I confessed that I had spent most of my 20s and 30s unattached. After the column was published, I heard from people around the world who also struggled with the shame of longtime singlehood.

We all have our stuff, or our thing. But many of us are also our own harshest critics. And as I contemplated my vegan friend’s question, I figured out what was bugging me—the word “hide.”

If she didn’t want to get into the details of her diet, there was nothing wrong with that. We aren’t obligated to provide a complete medical/psychological/financial/romantic history at the first coffee meet-up, or even the fifth or sixth romantic dinner.

But there’s a difference between hiding information and simply keeping it private. Hiding is an act of shame; keeping something private is an act of self-respect.

The person you’re meeting for margaritas isn’t entitled to all your most sensitive information now or maybe ever. Sure, of course, when and if the relationship gets serious you’ll want to let this person know that you have diabetes or were once or a member of a religious cult.

When do you do that? Jones can’t say, and neither can I. You do it when you think it is time, or maybe a little before. Of course it will be scary. Love is scary; that’s the deal.

“Vulnerability is what love is all about,” writes Jones. “And vulnerability involves yielding control, revealing weakness, embracing imperfection and opening ourselves to the possibility of loss. Only when we open ourselves to the possibility of loss can we allow for the possibility of love.”

its not you sara eckelFor my part, I waited a month before telling a cute copyeditor named Mark that I hadn’t had a boyfriend for eight years. His response: “Lucky for me. All those other guys were idiots.” That was eight years ago. We’ve been together ever since.

Sara Eckel is the author of It’s Not You: 27 (Wrong) Reasons You’re Single. You can get a free bonus chapter of her book at You can also find her on Twitter and Facebook.

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