Boomerangst: Turning Dilemmas Into Discoveries – Taking Online Relationships Offline

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When is it time to meet someone in person? Tips for taking your online relationship offline.

Q. I’ve been having an online relationship for over four months with someone I met on a dating site and we also talk on the phone. Both of us have been alone a long time. The first time we were supposed to meet (he lives a short distance away) I chickened out. The second time he chickened out. The problem is I’m getting tired of the e-mails, phone conversations and dreaming about this person. I’ve made no demands nor have I invited him over. I feel if he really cared as much as he says he does, he’d want to meet me in person. He’s very open and honest and answers any question I put to him, so I know he’s not married or living with someone – but I just don’t know what to do now. How can we move this to the next stage?

Alana, Calgary


A. By being brave, that’s how. You’ve been waiting plenty long enough. And four months?! Even four weeks is too long to wait to meet somebody in person, according to Julie Spira, the U.S.-based online dating expert and best-selling author of The Perils of Cyber-Dating. It’s especially long when you both live so close.

Julie says it’s clear that what you’ve got here is a “digital pen pal and a phone friend.” This means you’re in ‘the friend zone.’ That’s fine if that’s all what you want, but it sounds like you’re after more.

“The first few interactions in everyone’s case in online dating absolutely set the tone for your potential relationship,” says Julie, adding that by cancelling the first date he might have thought you weren’t serious and just wanted to be friends. And that set the tone.

So what can you do to see if a ‘next stage’ is possible?

Be bold and brave, says Julie. “Suggest a specific date and time to meet in person. Name a restaurant – not too expensive – and see what he says. Tell him you enjoy his emails and phone calls, but you’re ready to meet in person. If he says he can’t make it, get him to suggest an alternate date and time.” And if that doesn’t work, well, the writing is on the wall.

“Realize you’re in the friend zone and it’s time to find someone who does want a real relationship – which is the main reason people go online,” points out Julie, who speculates he may have already found someone else, or he may simply be after the ego boost of having someone of the opposite sex to talk to.”

If you can’t get to the next level with this guy, Julie figures you have two choices. You can either stay friends with him, while at the same time looking for someone who’s ready for a deeper relationship. Or, you can cut your losses and forget this guy so you can put all your energy into looking for what you really want. This is something only you can decide.

“But you have to start dating other people and stop putting all your eggs in one digital basket.”


Send Diane a brief description of your dilemma, along with your first name and where you live, to [email protected]

A professional journalist for more than 25 years, Diane Sewell has written for some of the top newspapers and magazines in Canada and is a baby boomer herself. Her new blog “Boomerangst: Turning Dilemmas into Discoveries” is interactive with readers and focuses on life issues – like aging, dating, second marriages, sex, death, family and fashion. Diane will use her expertise to find the right expert to help solve your predicament, unearthing kernels of truth and quickly getting to the heart of the issue.