Our Best (and Worst) Break Up Stories

As the song goes, “breaking up is hard to do,” even if you have the best of intentions. And with the upcoming holidays—aka Break Up Season—those shaky weeks preceding Christmas when people are most likely to peace out of their relationships, now is the perfect time to soak up advice on how to deal with the turmoil of breaking up with a loved one. That’s why we rounded up the best (and worst) breakup stories and tips from seasoned relationship experts and writers to help you with your breakup. Whether you’re the dumper or dumpee, you’ll definitely want to read these tips.

Breakup #1: Communication is Key

From Dr. Megan Stubbs, Sexologist and Relationship Expert

I was dating this guy for a few weeks. We met where most love stories take place nowadays: the Internet. He did everything right—he was respectful, he was funny, he held my hand, he kissed me in public, he surprised me, and the sex was fabulous.

In the beginning, the communication was great. We texted and called frequently, but as the weeks went on, he became more distant. I called him out on this and he apologized, blaming it on the fact that he was on the road so often (he was a professional athlete). Deciding that was a reasonable answer, I let it go. We were good for another few weeks and then suddenly he was gone. Ghosted. No response, not a phone call, or text, nothing. I was like, “Are you serious? “

My short tip to men on break-ups is that if you’re having doubts, speak up. Do not try to limp along in a relationship you aren’t feeling. Your partner can tell when something is off and if she calls you on it and you deny, you’re doing no one any favours. Communication is key in having a healthy relationship. Give you partner the respect they deserve and say what you feel. Don’t just disappear and call it good.

Breakup #2: Be Clear With Your Intentions

From Valerie Gibson, relationships expert, writer, speaker, media personality, author of Cougar: A Guide For Older Women Dating Younger Men and The Later Dater: A Guide For The Newly Single Woman Over 50.

I was dating long term a man who lived in another town, which was about an hour’s drive away, and we connected every weekend and whenever possible. I thought we were in love and would eventually move in together.

One day I got a telephone call from a woman who said she had found out I was dating her boyfriend! I was in shock, then, of course, big anger. So I got all the details from her—her name, address, telephone number—and told her I would drive there and we would talk.

Well, it was in the depths of a Canadian winter’s night. There was deep snow everywhere and travel warnings as the roads were “impassable” with “white outs”. But I still set out in my little sports car extremely determined to get there, even as I passed many cars in the ditches, accidents, police flashing lights etc. I just drove on past everything through whiteouts, through the blizzard, past police stops and amazingly finally reached her house.

She was an attractive student, younger than myself, and after talking to her, we shared our anger. She told me that she and my boyfriend had been living together! So I drove us to their rented house in the country. We then sat ourselves down and waited and waited. My (and her!) boyfriend finally came home late and he was drunk, but he went absolutely white when he saw the two of us there and sat down sharply, struck dumb and totally in shock.

I said very little—called him a few choice names, though—so did she, and we left together and I took her back to her mother’s house.

That was the end of my and their relationship and still, to this day, I don’t know how I managed to drive for an hour in a raging snow blizzard and wild winter storm in a small, light sports car and actually reach the other town. Looking back I think I was fuelled by very strong emotions and it just kept me going.

They broke up immediately—so did we—but it was a night I’ll never forget.

Neither did he, I’m sure.

Breakup #3: Kindness Can Exist

From Shannon Tebb, Matchmaker & Dating Consultant, Shanny in the City

Break-ups are the worst but can sometimes be for the best. I always remembered one of my old boyfriends telling me that “an ex is an ex for a reason.” There’s an obvious reason why things didn’t work out in the end. The communication died, you stopped being intimate, you found out your spouse cheated . . .The list goes on.

One break-up in particular that was handled the right way in my books left me feeling empowered rather then laying in bed crying for days. After we had the “we have to talk” chat and we agreed to end the relationship, he also sent me an email a day or so after. In the email he attached a lovely poem titled “Are You A Reason, Season or a Lifetime?” After reading this it was clear that he had been in my life for a reason, to assist me through a difficult time, help me make a big decision and be there for me. I couldn’t help feeling grateful for the relationship and everything it taught me. I asked myself could I have done things differently? Was it just bad timing? Rather then over analyzing every detail I decided to refer back to this poem whenever I was feeling sad and simply be grateful for the relationship and him even though he was no longer in my life. This is my best breakup story. They do exist.

5 More Tips

1. Don’t ghost. With our connection to each other through social media Facebook, Instagram, Twitter, Snap Chat, etc and daily text messages our relationships, even brief ones can often feel much more intimate than they really are. So when a guy disappears with all this connection its tough for a lot of women to deal with. We’re often left spinning, wondering what happened. Did we do something wrong?  Is there something wrong with us? Was there someone else? Never quiet getting the closure we need.

While it’s easy for guys to disappear, avoid an uncomfortable conversation or the guilt of a breakup it doesn’t mean you should. Men don’t often need closure in the same way that women do but if you’ve been dating for a few months and it isn’t working anymore she at least deserves a conversation with you. The general rule of thumb is, if it’s only a few dates a text is ok, if you’ve been dating for a few months, breaking up in person is the right thing to do. (Deanna Cobden, Dating Coach, Date Works)

2. Limit social media and take a virtual “friendship” break from your ex. Most of us are tempted to check in on our exes, but while the breakup wound is still fresh, it can do more harm than good. Not only do exes craft posts specifically designed to sway your emotions, but also our emotional interpretation of digital messages and posts has been shown to be inaccurate. Instead of living through social media, get out and push your comfort zone. Go for a hike, try ice climbing or sign up for an archery tag game with friends. Engaging in new and challenging activities can help to take the place of any passion you might have temporarily lost during/after the breakup.

3. Trust the research. Studies show that we tend to overestimate the amount of time it takes to get over a breakup, so remind yourself that the process won’t be as long or as arduous as it might seem in the few days and weeks. On average, it can take eleven weeks before you realize that the breakup was, in fact, a positive outcome.

4. Talk about your breakup or write down your thoughts and feelings. Conventional wisdom may suggest that we should distract ourselves and avoid thinking about an ex in order to move on, but a degree of reflection has been scientifically shown to speed the healing process. A study of 210 participants who had recently undergone a relationship breakup found that discussing the breakup via interviews and questionnaires accelerated the healing process. Consider setting a time limit for this reflection to ensure it doesn’t drag on indefinitely. I suggest allowing yourself to think about the relationship freely for two weeks and then weaning off gradually over the following two to three weeks setting time limits to compartmentalize your worry time.

5. Own your emotions. If you’re feeling sad, lonely, abandoned and/or anger, know that these feelings are likely a part of the transition process. By acknowledging your emotions, you can transition to the next phase in which you’ll likely feel relief, freedom and excitement for the next chapter. (Dr. Jess, VigorMan’s Sex and Relationship expert)

Brianne Hogan is a freelance writer based in Toronto, something of a humorist, and considers herself more Bridget Jones than Samantha Jones. Though she won’t reveal which parts, she will admit to liking emotionally unavailable men and drinking lots of wine.  You can follow her on Twitter  @briannehogan.






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