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Not So OK, Cupid

In a small town, online dating can sting in big ways

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It happened when she was messaging a 40-year-old man who lived locally. "I saw something that I see all the time, but it was the first time I noticed it," she recalls. "At the very bottom of his page it said [the age range] he was looking for: 18–25."

"When you're older and you're online, it tends to not go your way, because men your own age tend to look for younger women," Margot, 42, agrees.

"If I'm out in the real world, I'll get hit on by guys my own age and guys younger than me, somewhat frequently. I seem to get attention. But online there's a different set of qualifications."

And according to the three women, this disconnect between reality and internet fantasyland can get much, much stranger.

There's the goth guy who likes to walk women around town on leashes. The guy who's constantly changing the city where he supposedly lives. And then there was Kate's boyfriend, who created a fake OkCupid account while they were still in a relationship and secretly tried to get her to cheat on him with . . . his online self.

"Every single section in there was catered specifically to my profile," she says. "Like [he wrote about] this obscure East Bay band, Our Lady of the Highway, which hasn't played together for, like, 10 years. He sent me four messages within a 12-hour period, two really late at night and two really early in the morning, begging me to contact him."

Two months later, she says, he admitted what she already knew—that it was him.

"That kind of spooked me," she says. "It made me wary, like anybody can have an OkCupid account. It really freaks me out that someone could just be out there to fuck with you."

Louise used the site for six to eight months—dated someone for a month, someone else for two months—and then met a guy in real life. That lasted a year, and then she went back to the site. Her second time on OkCupid—post–difficult breakup—was wildly different than her first, and she only used it for 10 days.

"I just kind of wanted some distraction, but I understood what my friends had been saying about it," she says. "Before, I had just been having fun. But the second time, I was like, 'I don't want to put myself out there. I just got stomped on.' It's scary to get disappointed so many times."

"I didn't have a negative experience with it," says Margot, who was only on the site for roughly a week. She had one date, she says. "I just kind of realized that I didn't really feel like dating online. It felt like a lot of work. After you go on the date, then you have to think about, well, are they going to call me, or is this going to turn into a relationship?"

"When you just want to have fun, and you're not looking for Mr. Right and the clock isn't ticking and you're really open-minded, that's the best way to use online dating," says Louise.

But after several years in the real dating world, she says, "It just wasn't fun anymore."

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