How to start dating again after ending a long-term relationship

The average length of a marriage in Canada is about 14 years, according to Statistics Canada. Getty Images

Dating after ending a long-term relationship can be a scary thing. Just the thought of jumping back into the dating pool after being out of the game for so long can stir up emotions and induce anxiety.

It can also trigger uncertainty and doubt, leaving you with questions about yourself, your future and your love life.

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“It takes time to get over a breakup,” says sexologist and relationship expert Jessica O’Reilly. “You can’t think yourself happy, and even though there are steps you can take to boost your mood and shift your life, you can’t eradicate negative emotions. The first thing people can do is to allow themselves to feel sad, angry, hurt, betrayed, jealous, insecure — to really sit in and lean into those negative emotions because when we acknowledge them, we can start to reconcile them and come to terms with them, get over them and move on from them.”

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“After a breakup, I think you need to do a dating detox and just work on yourself and self-assess,” adds matchmaker and dating expert Shannon Tebb. “Plan a weekend getaway with friends and just focus on you for a while.”

And it’s that time you take for yourself that will help you move onto the next stage, O’Reilly and Tebb say.

But how do you know when you’re ready to move on and date again? With the rules of the dating game having changed since you last played, where and how do you even begin?

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O’Reilly and Tebb share their suggestions on how to navigate those uncharted dating waters for those who are little rusty and want to try again.

Hold out until you feel ready

While it may seem like you’re the only one who’s going through a breakup and struggling to find their dating “sea legs” again, you’re not.

According to the latest numbers from Statistics Canada, the average length of marriage in Canada is about 14 years and the national divorce rate is 48 per cent. It’s safe to say there many others out there who are in the same boat as you, each of them asking the same questions.

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Perhaps among the most popular bit of information people want to know is how long it will take for them to get over a breakup, and when should they start dating again.

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Some say it takes half the length of the relationship to get over your ex. One report from earlier this year by marketing research company OnePoll says it takes an average of 18 months.

However, O’Reilly and Tebb say the amount of time it takes to get over a breakup really depends on the individual – but there are signs to pay attention to that’ll help let you know when you’re ready to move on.

“You probably don’t want to move into another relationship if you’re still caught up in comparing it to your old relationship,” O’Reilly says.

“It happens on occasion, but if everything about the new relationship is measured against the old relationship, you probably have more work to do getting over the other relationship.”

“You’ll feel like you can really give your time and heart to someone,” Tebb says. “You’ve made time to fit somebody into your schedule — you’ve healed yourself, so you’re not feeling those negative emotions. You’re in a good mindset, you’re feeling positive, and you’ve taken a break and taken care of yourself. You’ve learned from your past relationship and you’ve forgiven your ex-partner and accepted that the relationship ended.”

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Once you feel you’ve checked off all those boxes, you may be ready to move on to step two.

Build your personal brand

The next step, Tebb says, is to sell yourself.

Much like any business or entity out there, you need a personal brand that will help tell people who you are and what you’re looking for.

“Now that you’re out there as a single, you have to brand yourself and think about what makes you unique from all the other singles out there,” Tebb says.

“Why would somebody want to date you? That’s going to really help you increase your confidence. Also think about what your strengths are, your attributes, what you can give to somebody and what makes you great.”

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By doing this, you’re not only trying to sell yourself, but you’re preparing yourself for upcoming dates. Knowing the answers to these questions, she says, is great practice and can help you facilitate a conversation with nice back-and-forth flow.

Notice tricky emotions

We’ve all had that moment after a breakup when we felt like we missed the other person. Just when you feel like things are getting better, or you’re in a great place, old feelings start coming back.

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These feelings are normal, O’Reilly says, but they may not mean what we think they mean.

“[These feelings] don’t necessarily mean you’re not over the person and that you want to be with them again,” O’Reilly says. “It could be indicative that you are struggling with what happened in the relationship or something from the breakup that’s upsetting you.”

She adds, “Maybe it’s the way you behaved — what you said or didn’t say. So sometimes if we look to those aspects of the breakup, we learn more about ourselves and we come to acknowledge that we didn’t really want to be with that person anyway.”

Pick your path

There are many ways in which people can find dates nowadays — it just depends on what you’re comfortable with.

“Find out what dating platform works best for you,” Tebb advises. “Is it online dating? Working with a matchmaker? Going to speed-dating events? Figure out what your plan is.”

If you prefer the old-school method of meeting someone through friends, don’t be shy to let your friends know your newly single status and that you’re ready to date.

“Say you’re at a dinner party with a bunch of married people and you’re the only single person, if someone asks, don’t be afraid to tell them you’re single and ready to date,” Tebb says.

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“You never know, that person might have a cousin or know someone who would be great for you.”

“If you don’t speak up, people aren’t going to know,” O’Reilly adds.

If there’s one thing that O’Reilly wants people to stop doing, it’s the idea of finding “the one.”

“There are many possibilities of ‘ones’ you can be with — not just one person,” O’Reilly says.

“However, don’t be discouraged if you meet a few people who aren’t good matches for you. You have to go through a few before you do find someone who is a decent match.”

READ MORE: Taking a break from your relationship? Here are the dos and don’ts


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