Knowing When to Start Dating Again

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I walked out of a coffee shop last week, listening to my coworker discuss his fears and apprehension regarding the dating scene. Divorced and hurt over previous relationships, he was firmly closed off at the suggestion of setting up a Match account or a dating app to get back on the scene. I promised that we’d continue the conversation later and the question of, “when should you start dating again” marinated in the back of my head the rest of the day.

After a divorce or a serious relationship, when should you start dating again? What does it mean to feel “ready”? Is it multiplying how many years you’ve spent in your relationship by half to equal a years/months on when you should get “back out there”? Why do we resist so much? When do we know it’s time?

It’s a difficult, emotionally-charged decision to be making and many of us don’t know when we’re “ready” to put ourselves back out there, juggling feelings of nostalgia from previous relationships, anxiety from the past pain and ultimately fear of the unknown. We wonder whether the next man we date will be better or worse than our ex. What ultimately scares us more? Is it letting go of our ex and finding someone even more amazing? Or are we scared that we won’t find someone else that surpasses the love we lost and be forever hung up on “what could have been”? Are we worried about rejection? Are we resistant about starting something new with a complete stranger, sharing parts of our souls, lives and body that are so accustomed to loving one person? The answer was a resounding yes to all of these questions for me. I was scared about everything when it comes to dating.

I was scared to open up again, to let someone in, to trust again, to feel emotions again after going through the storm, destruction and recovery of finding and losing love earlier. It would be like asking New Orleans, “are you ready for another possible hurricane? The next one may be more intense”.

Dating after a serious relationship is scary.

But you know what’s even scarier?

Being a relationship that is horrible for you and staying with it because you think should.


The ultimate push for me was my 28th birthday last week. I sat in my studio apartment, in an oversized t shirt, looking at the boxes of presents and delivered flowers, holding a cup of coffee. Look at that, I thought, I’m twenty eight.

In a few years, I wanted kids, giggling toddlers with big smiles and open arms. I wanted a rescue dog and a warm home filled with love and laughter. I wanted a husband that stood by my side, who supported me, whispered sweet nothings in the mornings with our bodies entwined. I wanted us to build a beautiful life together.

To have that later, I needed to take action to begin dating now.

I took the jump. I took out my phone, downloaded a dating app and then began meeting men in New York city, with the scent of roses in the air and Amazon prime birthday boxes littering the apartment floor.


Let’s go through the decision process of beginning to date again.

The first and most important decision I had to make is that I want to move on. According to a national surveys, most couples break up, get back together, and break up again multiple times before deciding it was enough. Yes, it may work out if you try again with your ex, but I promise it won’t work if you’re both going back to the same relationship, doing the same fights and arguments over again, expecting a different results. That’s insanity.

In the words of Tupac, You can spend minuteshoursdays, weeks, or even months over-analyzing a situation; trying to put the pieces together, justifying what could’ve, would’ve happened… or you can just leave the pieces on the floor and move the fuck on.”

There is a good reason why you two broke up. Understand it and remember it for the upcoming months that will ironically replace the bad memories with all the best times, begging you to recall what went wrong in the first place.

The second thing I recommend is going to therapy. I’m serious. Go to therapy. I cannot advocate enough the benefits of getting counseling after a traumatic break up. Having a kind professional sit across from you, navigate through your thoughts, redirect your thinking into a healthier, more positive direction, will do wonders for your recovery and subsequent relationships. Don’t bottle it all in, let it fester and ooze into future relationships. Get it out, deal with it and then let it go.

After deciding I was moving on, got therapy, I fixed other parts of my life that I neglected. A break up is a perfect time to rebuild yourself. I got in shape. I quit consulting. I moved across the country. I learned how to cook. I began writing consistently. I’m applying for better jobs. I am completely invested in improving myself.

The goal of:

  1. Letting go,
  2. Finding healing and then
  3. Creating progress in your life

is that sooner than later, you’ll be in a good place.

You’ll feel strong again. You’ll feel happy. You’ll stand completely alone and feel whole. You won’t need someone to call you at night. You’ll fall asleep soundly alone in your bed, lying starfish in pristine white comforters. You won’t need him to remember your birthday. You have enough love in your life to replace his presence. You’ll start setting higher goals, higher aspirations and higher vibrations, already surpassing the person you were or could have been with him.

You begin to move forward more confidently, with less glances back at your past. You stop settling. You cut out more and more toxicity out of your life, without apologies or second chances. You ask for more because you know you deserve more. You shut down the bullshit, the lies and the manipulation because that negativity has no place in your life. You vibe easily to meeting people because you’re open again. You act out of kindness and self respect, because you no longer carry anger, resentment and guilt in your heart. You volunteer for a cause and you give back without expectations because you have so much more to give. You’re cooking for one and it’s one of the best meals you’ve cooked. You’re learning and you’re growing. You feel your world expanding, capturing more than you thought was possible.

You feel free, running across the Manhattan bridge with the wind in your hair, train tracks to your right, feeling as though you can run forever.

You’re limitless. You’re never ending. You’re strong. You feel the world rush around you, like a river, and you’ll be standing in the middle of it, completely grounded and centered with who you are. You’re back, but better and stronger than ever.

That is when you want to start dating again.

There is no timeline. No formula. No checklist. There is a feeling — when you feel so completely happy, secure and confidant in your own company and life — that tells you, “hey, I think you’re okay now”.

You’re ready.

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