Dating Secrets: Why Confessions Are Made on the Third Date

Is your date a convicted felon? Secretly married? On meds? Hannah Seligson on the secrets people reveal during courtship—and why they usually confess them on the third rendezvous.

“It was about the third date my freshman year in college, and I’m lying in bed with this fantastic guy,” says Ellie. “We talked politics and made fun of each other and he took these great black-and-white photographs of me. In short, I was crazy about him.” Then, for some reason, Ellie went for the big reveal: she told him she was still together with her high-school boyfriend. “Unsurprisingly, he broke up with me,” she says. “I was crushed. He’s still totally dreamy.”

Welcome to the third date, that moment on the courtship trajectory when the truth comes out about STDs, personal hygiene habits, secret significant others, family backgrounds, and, yes, their real age. Anecdotally, the third-date confession has become so legendary that some people have come to fear the third date for what they’ll learn about the up-to-now-wonderful person smiling at them from across the table.

“One girl said to me, ‘If I didn’t take my Xanax, I don’t know what I would do.’ Another started dishing about the eccentricities that required her to be on Klonopin.”

“I have a friend who, on the third date, told the guy she was seeing that she had herpes, in anticipation of the fact that they might sleep together that night,” says Elizabeth, 30, a clinical social worker in New York. “It turned out he did too,” so it didn’t matter—a near miss of a confessional catastrophe.

This points to the fact that for many people, the third date is the first date for sex, which may be part of what prompts such third-date confessions. (The rule goes something like this: If one party declines sex on the third date, it’s a sign the relationship is going nowhere.) This makes the third date a natural moment to fess up about any contagious diseases. But it also seems to lead to a more generally disclosure-based date, in which confessions about felony convictions and plastic surgery make their debut.

“It’s oddly funny how people give away what prescriptions they are taking on a third date,” says Dan, a 25-year-old filmmaker in Los Angeles. “It’s happened to me on four separate third dates. One girl said to me, ‘If I didn’t take my Xanax, I don’t know what I would do.’ Another started dishing about the eccentricities that required her to be on Klonopin.”

Some details go over better than others. “When women tell what meds they take, it’s usually a big turn-off,” says Dan. “It’s this kind of forced intimacy.” On the other hand, says Dan, “If a girl I was on a date with told me she was from a broken home, that’s the kind of thing I feel like I would appreciate hearing about on a third date.”

Not everyone agrees.

On a third date with a former co-worker, Jessica Massa, 26, co-founder of the online dating forum, learned that both of his parents were drug addicts and that he had been supporting them (just their bills, not the drug habit) since he was 16. “He revealed this along with similarly deep and complicated personal and family issues,” says Massa. “It was intense to say the least.” A fourth date, it turned out, was not in the cards.

The tone, tempo, and type of information revealed in a burgeoning relationship can get complicated. Is there ever really a right time to tell someone you are dating you never finished high school, that your father is a Satan worshipper, or that that sex tape of yours is still making the virtual rounds?

“I generally advise people to hold off on revealing information until things have become exclusive and serious,” says Dr. Diana Kirschner, a New York-based psychologist and author of Love in 90 Days.

There are, of course, caveats. “With STDs, plain old integrity means you have to reveal that kind of information before you become sexually active,” says Dr. Kirschner. “But for most other things, you want to have enough of a relationship that has grown between you two to weather these disclosures.”

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Still, the third-date reveal can go either way. It can be a bonding experience, or it can be like dropping a concrete block on the surface of a still-delicate new romance.

Elizabeth, 30, has been on both sides. “On my third date, with a guy I ended up dating for many years, he told me he was 27, not 24,” she says. He worked in an industry where there was a high premium placed on being young. “His age became a running joke between us.”

However, not all biography goes over so well. When Elizabeth told a guy on a third date that her grandfather had been the CEO of a major international conglomerate, she never heard from him again.

Why is the third date the moment in the dating arc when people decide to get real? Why not the second date? Or the fourth?

Psychologically, Kirschner says, the third date is a moment when you are just starting to relax. And comfort can quickly morph into the impulse to reveal embarrassing or scary information. “It’s an unconscious wish to be accepted,” she says. Disclosing information, particularly if it’s personal, is a time-tested way to connect.

Rebecca Wiegand, 26, who, along with Massa, co-founded, told “Dylan,” on their third date that she has a “gaggle,” a group of guys in her life that fall somewhere between friend and more-than-a-friend. “Dylan was definitely in my gaggle, and we had this whole meta conversation about the concept,” says Wiegand. Following that little chat, however, Dylan completely disappeared.

“Maybe he thought I don’t owe this girl anything because she has this gaggle of guys,” Wiegand says. “I can’t say for certain.”

What is certain is that without context, a bit more history, and a rapport that extends longer than coffee, two dinners, and a movie, it’s likely that comments, idiosyncrasies, and personality tics could be misinterpreted. “The revealing that happens on a third date can backfire terribly,” says Dr. Kirschner. And yet daters keep doing it. Here’s a theory as to why: There’s something empowering, even if it’s only temporary, about saying early on, before anyone gets too emotionally invested, “This is who I am. Take it or leave it.”

Case in point: When Christine, 27, who works in the media industry in New York, went on a third date with a freelance journalist, he decided to show her a different side of his personality. One night, after a few drinks, they went back to his apartment. They stumbled through the dark into his bedroom. The next morning, she got up to use the bathroom, only to find his living room crammed to the rafters with newspapers, magazines, and pamphlets dating back to the Bush administration. (This was in March.) “He was a hoarder,” says Christine. “It was near horrifying. There was a big bowl of Halloween candy sitting out on the counter that he said was left over from his Halloween party.”

“I think that he was trying to delay the inevitable by not having me over sooner, but then, by our third date, it kind of had to happen,” says Christine. “I’m sure he had some sense that I might not be comfortable with his ‘ways,’ but that if we continued to see each other, it would have to come out eventually.”

Many of the names in this article have been changed.

Hannah Seligson is a journalist. Her book, A Little Bit Married: How to Know When It’s Time to Walk Down the Aisle or Out the Door, which spotlights and uncovers a major trend in dating today, the long-term unmarried relationship, was published by Da Capo Press on Jan. 15.