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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. 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.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?One night, after a few drinks, they went back to his apartment. 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. 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.Disclosing information, particularly if it’s personal, is a time-tested way to connect.Rebecca Wiegand, 26, who, along with Massa, co-founded wtfisupwithmylovelife.com, 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.
She rejected any service that plunged women too deeply into a relationship at its outset, like one based entirely around travel companionship.
“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.
“It sounded exotic,” she admits, “but I don’t have a Liam Neeson in my life to come track me down!
” The service she chose allowed her to dream big, while approaching prospective matches with the same cautiously optimistic deliberation she’d bring to any new relationship.