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Get Out of the Online Email Loop!

If you're exchanging endless emails that never lead to dates, we'll explain how to break the cycle (Sponsored by

stuck in the email loop

You save him as a “favorite,” and he sends you a wink. After that, a string of emails follow, each more enticing and engaging than the next. But while the growing number of emails, texts, and flirty DMs whet your appetite for a face-to-face date, the object of your growing affection seems content with your ever-blossoming virtual relationship.

Welcome to the world of the online email loop.

“It’s really weird,” says Dan N., a 29-year-old comedian from Manhattan. “The thing is, I would imagine that if the person responded to you, there would be some sort of interest in getting together. But it doesn’t happen every time. I’ll be emailing back and forth with a girl and I’ll ask, ‘Hey, do you want to get together for coffee or a drink?’ But then you don’t hear anything for a while. Or suddenly, she’s really busy this week and next week, but maybe she can do it in two weeks. It’s like the other person keeps pushing it forward and pushing it forward, but it never actually happens.”

Why people drag their feet in taking things offline

Suzanne Schlosberg, author of The Curse of the Singles Table, says this kind of online foot-dragging behavior drove her crazy back in her dating days. (She’s now married to someone she met on a few years ago)

“I found that endless emailing was ridiculous, because there’s no way you can predict chemistry in person based on your shared chemistry online,” Schlosberg says. “One person’s voice could annoy you or a guy may remind you of a horrible ex-boyfriend in person. I had a lengthy email affair with this one guy and we went back and forth for a month, emailing daily. I was convinced he was Mr. Right, but when we finally met in person, it was not a match. But the chemistry was uncannily amazing online.”

Damien P., a 44-year-old marketing representative from New York, says he thinks both the sheer number of people using online dating sites — plus all the bells and whistles now available — contribute to delays when it comes to meeting people face-to-face. “I think many people just become content with endlessly surfing and comparing people,” he says. “And all the chat tools and games and questions for determining compatibility are all very interesting, but also make it more likely that people will be content to do just that — to keep things online.”

Schlosberg says many people put off the inevitable first meeting because the idea of dating a virtual stranger is just too daunting for them.

“It’s nerve-wracking and it takes practice,” she explains. “But it’s not going to get any less stressful just because you’ve emailed or texted back and forth 50 times.”

Why delay meeting someone in person?

Dan N. says that he sometimes wonders if the women he “meets” online aren’t looking for relationships so much as something to keep them from nodding off at work. “I suspect that some of these people are in boring office jobs, just sitting at a desk with nothing better to do,” he says. “They just want pen pals, so they get into email exchanges with guys. Or maybe it’s just that they’re getting hundreds and hundreds of responses and they can’t keep up. That could be a factor. Of course, another possibility is that I’m just really boring.”

Los Angeles psychotherapist Nancy Irwin thinks that if people are toying with potential dates just to kill some time, the reasoning behind it probably goes deeper than that. “These women may have anger toward men and are getting back at them by stringing them along,” she says.

More likely, though, she says the incessant emailing and excuses likely indicate having intimacy issues. “Some people are really just into the fantasy of a mate,” Irwin says. “And they feel like if they actually meet someone, that person will run away in horror because they don’t think they’re smart enough, good enough, or think that they’re socially inept or whatever. It’s more comfortable to not see the person behind the emails. They can control the relationship that way. They hold all the cards.”

phone with email notification

Sexual fears can also be a driving force behind an “elationship,” according to Irwin. “People are afraid if they get too intimate, they won’t be accepted, so this is a way to delay that and prevent it,” she says. “They feel like they’re in a real relationship — they get all this attention, people see them getting texts and emails, they have society’s stamp of approval that they’re in a relationship — but they don’t have to deal with the intimacy factor. They don’t have to deal with their own sexual fears or admit any of their deep, dark secrets.”

A person who relentlessly pursues you online but never seals the deal in person may also be married or involved with someone else, Irwin warns. “It could be someone who’s bored in a relationship and doesn’t know how to recapture that honeymoon phase, so he or she is constantly reaching out and enjoying the fantasy of being with someone else,” she says. “Then, this person doesn’t have to look at the reality of his or her own situation.”

Set a personal timeline for moving past email recently asked the question: What’s the average email exchange time between online daters before arranging an in-person date? Out of the poll’s more than 4,000 respondents, 30 percent said they emailed back and forth for three or more weeks before meeting, 43 percent emailed for one or two weeks before getting together in person, and nearly 28 percent sent out two or three emails at the most before making a date.

Regardless of whether you prefer to exchange three or 300 emails before meeting face-to-face, Irwin suggests setting some ground rules.

“Have a sense of humor about it, but tell the person you have a policy of exchanging only so many emails, then you talk on the phone, then you set up a coffee date,” she stresses. “If the person can’t deal with that, then he or she is delaying it, and you may want to take that as a warning signal that this person could be delaying a lot of other things in a relationship. Have your policy in place, and if your online crush keeps delaying, then move on.”

Schlosberg says capping her email exchanges helped her reach her goal: finding a marriage-minded mate. “I learned fairly early on about the endless emailing, and there’s no value in it,” she recalls. “You do need to go back and forth a few times, but really, just a few should suffice. I set the number at five emails. I felt like that was enough to figure out a match’s level of inquisitiveness and get a feel for that person’s sense of humor. That was enough to figure out whether someone was worth meeting or not.”

But Stephanie W., a 51-year-old marketing company executive from Dallas, believes the emails do have to be substantive to take things any further. “The quality of the email definitely counts,” she says. “When people are trying to be revealing and honest, that means a whole lot — certainly much more than if they just email, ‘How was your day?’ Those people are blowing and going. They’re talking to a bunch of people.”

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