Dating After Divorce

Dating After Divorce

Five things you need to know.

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If you think divorce is hard, try dating once it?s all over!

OK, that?s a little dramatic. For many of us, divorce can be one of the most difficult life events we endure.

I have been separated for more than three years. Before that, I was with my ex-partner for the previous 14 years. That?s a long time and a big change.

Breaking away from the habits and routines formed by all those years together was challenging. I felt a loss of identity. Who was I without my partner? What did I want? Could I succeed on my own?

The answers to some of these questions took a long time to find. I?m still waiting on others.

Divorce throws your life upside down. It shakes you up like a snowglobe, and you have no idea how all the pieces that you once were will settle.

And this is complicated by the fact that most of us want some kind of partnership (or partnerships ? plural ? which I don?t think is for me, but to each their own!).

If you were in a long-term relationship like I was, the dating world can appear absolutely terrifying. I had never used a dating app. I hadn?t been on a date since I was 18 years old. I didn?t make new friends easily. I didn?t know what I wanted. I was shy.

I went on my first date about 6 months after my separation. Looking back on it, I wasn?t ready. Not even close. I had some reservations about dating, but I thought, To hell with it, what do I have to lose?

Today, I?m grateful for that brief display of bravery demonstrated by my past self. Dating has been an eye-opening experience for me and one hell of a ride. I?ve learned so much about myself in the process. And I?m so grateful to every person I?ve gone on dates with, who bravely shared with me some part of their journey.

Here are five lessons I learned along the way.

#1 You?re going to be insecure

Going on a date is a nerve-wracking experience, especially if you?ve only chatted with the person on some kind of dating app.

What do you wear? What if it gets awkward? What if they don?t look anything like their pictures? What if you have nothing to say? What if you embarrass yourself? What if they make you uncomfortable? What if they don?t like you? What if you know it?s not going to work within the first five minutes?

There are exactly 13,875 questions you can ask yourself before going on a date. Trust me ? I?ve counted. And every one of them can drive you insane.

Because I have no interest in having a psychological meltdown, there are a couple of things I?ve found useful to remind myself before going on a date.

  1. Each date is an experiment. You have nothing to lose, and potentially a lot to gain. Treat it as such. If things to wrong, correct it next time. If things go right, make note of it.
  2. This is a job interview, and you are the interviewer. We tend to focus on ourselves because we want people to like us. But, it?s better to find someone worthy of your time, not just someone who likes you. So, figure out whether you like them!
  3. Be grateful. Be grateful for the opportunity to meet another human being in a psychologically vulnerable position. They are opening themselves up to you in an unusual way. Don?t take that for granted.
  4. Check your expectations at the door. There is no need to go into a date with sky-high expectations, or the opposite. Instead, just go with it. Who knows, maybe you?re about to find your new best friend.

#2 You?re going to have awkward conversations

Let?s be straight for a minute. People are awkward AF. You, me, everyone. And then you add some fear, anxiety, and tension to the mix and BAM! you?ve got a disaster just waiting to happen.

Unfortunately, there?s not a lot you can do about this. Sometimes you click with people and sometimes you don?t. If you don?t, awkwardness is surely to follow. But, that doesn?t mean you can?t do anything to alleviate at least some of the awkwardness.

My way out of less than ideal dates is to simply ask questions. I?ve found that once I get people talking, things tend to calm down. Fortunately for me, I?m more of a question-asker than a talker, so it works out well. But, I don?t just ask question after question like a robot. I try to empathize, I try to relate, I try to understand. By inserting a little bit of myself into the questions, it opens up the opportunity for the other person to ask questions, too. That being said, some people aren?t very good at asking questions, so they?ll mostly just talk about themselves. That?s still better than awkward silence!

I also genuinely enjoy getting to know people. I?m curious about who they are and what they think. I?m curious about their passions. I?m curious about their histories. I like to make the most of the opportunity. So, try to think of it in this way. Each date you go on is an opportunity. You can learn something interesting from everyone. It?s just up to you to find it.

#3 You?re going to be irrational

When I finally felt ready to have a relationship, it was about a year and a half after my separation. How did I know?

Well, I met this person at work and it was a pretty standard ?courtship?. We started by chatting over email, which progressed to coffees at work, and then we began dating. What was interesting for me is that I finally felt unencumbered. My heart felt free, like a chord had snapped and it could just sail through the air.

That?s when I noticed the irrational feelings creeping into my mind. Funnily enough, I even connected the dots while it was happening ? I was finally ready to have a real relationship and I was excited. The problem was, that excitement carried over into the relationship, which meant I was pretty confused about my actual feelings for this person.

What I learned is that feelings lie. I?d feel some strong feelings for this person, but I couldn?t rationally justify them. Amazingly, that almost didn?t matter.

Thankfully, I?d been meditating daily for about 8 months by this time and was quite mindful of all this. I saw the ridiculousness of my mind and so I delicately and persistently maneuvered my thinking and feeling in another direction. This took weeks, but I finally got my head out of the clouds.

My point is, don?t be too hard on yourself for losing your head. You will. The biological drive to find a partner is a strong one. But, if you aren?t just looking for another future ex-partner, I?d suggest fighting this urge with some good old-fashioned rationality and mindfulness.

#4 You?re going to make people cry

This is a tough one. There?s no sugar-coating it.

Getting back into the dating world after divorce is complicated. It?s not just about finding the right person, it?s also about finding yourself. And I?m not sure you can do one without the other. Part of the journey of finding yourself includes dating people and getting to know what you want.

A little over two years after my separation, I met a truly wonderful person. She checked all the boxes. Every. Single. One.

At the end of our first date, we shared a passionate kiss, with snow quietly falling all around us. Suffice it to say, we pretty quickly fell head-over-heels for each other.

Almost 8 months went by before I knew something was seriously wrong. Not that it was a complete surprise ? we had talked about some uncertainty I was feeling a couple months earlier. But, this time was different.

We had just come back from an amazing 10-day trip together in the provinces of British Columbia and Albert in Canada. My feelings of uncertainty were very confusing, especially with the trip having gone so well and because they weren?t really about her.

But, I couldn?t ignore them, push them aside, or deal with them at a later date. Those feelings sat in my stomach like a dead weight.

Deciding to end our relationship was one of the most difficult decisions I?ve ever made. It had nothing to do with her, and everything to do with me. I wasn?t ready. There were things in my life that I still needed to do, things that I needed to prove to myself. And I knew I couldn?t do them with a partner.

Like the rest of our journey together, even our break up was beautiful. We sat in her place for nearly five hours. Waves of tears would wash over us, and then we?d just continue talking. It was terrible. It was wonderful. It was everything it should have been and could have been.

The thing is I don?t regret breaking up with her, even though it still hurts to this day, months later. It was the right decision. What I?ve learned is that there is nothing straightforward about life. For me, right now, I need to focus on myself. I need to put myself first.

#5 You?re going to need to put yourself first

Who are you? What do you want? What gets you out of bed in the morning? What gets your blood pumping? What makes life worth living for you?

These are age-old questions that we tend to brush aside because they?re hard to answer. No one wants to put in that kind of time or effort. But, we must.

What I?ve learned about relationships over the past couple of years is that they are not the be-all and end-all of life. My ex and I used to do everything together, which was both great and terrible. True, I have a lot of special memories with her, but there was an emptiness to all that time spent together because neither of us brought anything new to the table. We didn?t have our own experiences to bring a spark into our relationship.

Have you figured out what went wrong in your relationship? Have you acknowledged your part in the whole mess? How are you different now? What has changed to ensure that the same thing doesn?t happen again?

If you?re reading this, you?re probably divorced or separated. If you are, you need to accept that you played a role in making your current situation a reality. If you don?t, history will repeat itself.

Don?t let this happen. Instead, cultivate what you love. Explore. Learn. Grow. Don?t wait for a relationship to save you. It can?t and it won?t. Only you can save yourself.

The fact is, we have only one life to live. No one can live it for us. It?s up to us to ask the hard questions. It?s up to us to do the work.

So, get going and good luck!

Thanks for reading!


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