March 22, 2015

6 Things I Learned from Dating after Heartbreak.

Courtesy of Author. (Jamie Vasileff)

Everybody has that one relationship that breaks us so open, it nearly tears us apart.

The one that devastates us in a way that makes it seem as though feelings may not be possible (or even wanted), ever again.

But then.

One day.

Many, many, many months (or even years) later, we feel the sun start to shine on our cheeks again.

We start to notice the sunrise and the sunsets, and all of life’s beauty in between and think, perhaps, it’s time to crawl out of the ruin and open ourselves to the possibility of stumbling (or let’s be honest, Tindering) upon someone new.

This is where I find myself.

Thrust into singledom since the unexpected end of my marriage, nearly a year ago. Regardless of my internal reservations, I have started to traverse the complex and confounding world of dating after heartbreak.

This is where the real learning begins.

Here are six lessons I’ve learned from my re-entry into the dating world.

1. Too much, too soon.

Different people deal with heartbreak in different ways.

Some fly forward into the unknown, throwing caution to the wind, and scoop up the first person who is willing to fill the holes created by being hurt.

I had the same urges too, which led me to hurt someone who did not deserve to be emotionally thrashed around while I was figuring out how to pick myself up from devastation.

Latching onto someone when you’re so broken it hurts to breathe, can help triage the main wounds, but in the end, time and space is the only way to truly heal all that has been shattered.

Realize that if you do find yourself partnering with someone quickly “post break-up,” there is another person on the other end of this pair who isn’t beside you just to heal you.

Avoid the temptation of becoming “too much, too soon,” clinging to someone as a life raft.

Breathe. Feel your feelings.

Do your best to be your own life raft.

2. Go slow.

Dating is terrifying under any circumstances, but the terror is amplified exponentially when your wounds are still healing, you’re beyond vulnerable and still mending what was broken.

Don’t jump into the water before you’re ready. It’s obvious you’re not, so take all the time you need.

It was recently brought to my attention by a friend (who, just so happened to be my first official “post-breakup date”) that upon our initial meeting, it was apparent I was still very sad.

I knew enough not to be “that girl” who divulges all the secrets of recent break-ups on a first date, which leads me to believe that I was still carrying the emotional weight of my heartbreak with me, while trying to force myself into something I wasn’t quite ready to try.

Dating will absolutely be scary when you’re ready, but there is a difference between trepidation and complete and utter terror.

Go slow. Be kind to yourself. Have patience.

And, if you need a little bit more time, that’s okay too.

3. They might be rusty, but listen to your instincts.

I’ve always been a firm believer in trusting my instincts.

Unfortunately for me, I don’t always heed my own advice.

If you think the date you had from last Wednesday is avoiding you, even though they agreed to see you again “sometime soon,” they probably are.

And on the flipside, if you think your date’s flirty touches and thoughtful compliments are signals beckoning a first kiss, you’re probably right.

More often than not, the initial thought you have about the situation is probably the right one.

Trust yourself and your ability to assess the situation separate from the nagging thoughts of residual doubt that still lingers from your heartbreak.

As much as it feels like you have no idea what you’re doing, listen to your instincts.

You’ll be fine.

4. Embrace the awkward.

Most (okay, all) of the dating I have been doing lately has been online.

While online dating is both exhilarating and convenient, it is also very uncomfortable for various reasons.

There are so many facets and nuances to dating, the faster you can overcome the weirdness, the better.

Just go with it.

Essentially, the only things you know about these online matches is what they tell you through the veil of an iPhone app.

So, when the girl whose profile says, “only drinks socially” gets profusely drunk upon your first meeting, embrace the awkward.

Pay the tab and make sure she safely gets into her Uber.

5. Be you.

In the off chance you find a potential suitor, quit worrying about what certain things mean. Try not to stress over figuring out if you’re just “hanging out” or actually “dating.”

Push through the dread, show some heart and have those unnerving conversations when you feel the need.

Be honest, express your feelings and be clear.

No one really knows what they’re doing, so don’t expect yourself to be any different.

All you can be is you.

6. It’s not so bad after all.

It’s been almost a year since my heart was shattered.

I was devastated, broken and really freaking hurt.

While I’m still working on piecing myself back together, I know I’m actually ready to move forward. Dating thus far has been scary, fun, confusing, invigorating and bittersweet.

Life doesn’t always turn out how we hope, but starting from square one isn’t so bad after all.



Heartbreak is the Best Thing That Ever Happened to Me.


Author: Jamie Vasileff

Apprentice Editor: Brandie Smith/Editor: Catherine Monkman

Photo: Courtesy of the Author.

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