Advice Column: How To Date During Heartbreak

Advice Column: How To Date During Heartbreak
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Camila Cordeiro

Dear Chelsea,

After a terrible breakup I’ve taken on the form of being distant and not wanting to be in a relationship. I’ve even resorted to seeing people that I know are emotionally unavailable, or are attached to someone else. I know deep down that they are not what I need or want. I’ve wondered if I’m doing this out of a desire to not be attached in order to guard myself from being hurt.

I’ll entertain guys that live 2-13 hours away. For example, recently I reconnected with two guys from my past that I should’ve probably given more consideration to back then but now I entertain the idea of being with them because they live more than 2 hours away from me and with my work schedule it’s not possible to see them every day. This way I’m able to say that yes I’m seeing someone but not tied down to anyone because I’m not forced to see them all the time. Why am I functioning this way? Could it be that the last relationship I was in I truly thought would lead to marriage but instead he wanted someone to pursue his dreams and neglect their own? I have so many questions about why I’m emotionally detached and I’m open to going on the journey to hopefully answering all the burning questions.

Olivia Pope

Dear Olivia Pope,

All too often we complicate our dating lives because we just won’t accept where we are on the spectrum of coming into love, because we judge ourselves harshly and unnecessarily for chasing the people we are chasing and not choosing the relationships we say we are or think we should be after.

We complicate the pursuit by expecting ourselves to be further along than we are, by expecting ourselves to be ready for a love that eludes us, to be ready when the truth is we are exhausted and need a timeout.

My advice is, if your breakup has knocked the faith out of you, if it’s left you reeling and cautious and feeling, as you mentioned, like you don’t want to be in a relationship, then listen to your own warnings and slow everything down.

Trust me, just because you take your time doesn’t mean you are running out of time. It doesn’t mean you won’t end up in the very arms you so long to be held by. In fact, it’s only just the opposite. By going slowly, you give yourself the chance to fine tune your desires and develop into a woman who is discerning, who takes pleasure in trimming back on the frivolous. And that, by the way, is how you cultivate patience. It’s how you protect your heart. By no longer picking up dead weight. By no longer trying to turn every man into a home.

My advice is, rather than making a problem out of singleness by rushing so relentlessly out of it, by revisiting the men of your past and grabbing for those you admit to not even wanting, do what your heart needs you to do. Rest. Relax. Recover. Slow yourself down. Discover all the ways that not wanting to be in a relationship right now can benefit you.

Because you know what exhausts us more than the disappointment of a lost love and the race we’re in for a new one? The expectations we have for ourselves in the wake of that loss and in the midst of some race. The expectation, that is, to be somewhere we’re not.

Jiri Wagner

This is what I know for sure, we compromise our chances at getting to where we eventually want to end up by not copping to the fact that we are not ready to be there yet. By rushing toward what we want but are unprepared for, this is how we miss having what we are after.

If you want to fall in love, you have to first let yourself fall into place.

You have to let yourself be where you are. You have to forgive yourself if where you are is a place you don’t want to remain, a place that you don’t understand how you got to.

You have to accept—more than anything—yourself, that there are certain people you will be drawn to for the very reason that they buy you time to either recover yourself or understand yourself.

Don’t fight this or confuse it either. These relationships are useful but that doesn’t mean they are meant to last forever. The fact that they don’t last is equally important, too.

The reality is we are almost always lured in not by the man himself but by the experience we predict his company will offer us.

There is no harm in this either as long as we are honest about the experience we are after and going after the experience we are most in need of at this time.

It’s important to keep this in perspective, that to find love, you have to first grow into it.

My advice is, rather than focusing on the right man for your future, focus on what and who makes sense for right now. Focus on the experiences you need in order to grow into the woman you want to be, only part of which is a woman who’s not only ready to be with the one but is ready to be the one.

Don’t judge yourself for the experiences you need and choose. Don’t judge yourself if a man who is five hours away appeals to you because seeing him lets you reward yourself on the weekend after focusing on piecing yourself back together during the week. Again, if you know what you are doing and are upfront about doing it, where are you going wrong?

My advice is, be honest with yourself about the choices you are making. Invest your heart in discovering who you are and all you are made of, on knowing what it takes to become more of yourself. Do this and you will have an easier time making better choices in dating for the very reason that you will be confident honoring who and what you need.

This is what dating is all about after all. It’s about pushing ourselves into a series of firsts, of uncertainties and extremes, of hangups and obstacles, into a series of lessons.

Dating is about preparing ourselves to be the person who can love and be loved through better and worse. And because this doesn’t just come naturally, this is exactly why we need dating to teach us:

To teach us how to love during distress and remain lovable even when we disappoint.

To teach us how to be tested and tried and have our patience worn.

To teach us what it feels like to receive an affection that feels incomplete and give a love that’s undeserved, what it feels like to co-create a passion that burns out fast.

Dating is designed to show us the kind of person we want to be left with, and in that process should prepare us for the possibility that that person could be ourselves, solo and alone.

Manuel Del Moral

My advice is, look at dating as a series of stepping stones. Don’t leap across the river, take your time and step into it.

Look at every person you rub up next to as a necessary teacher. Don’t try to pull love out of them. Try to sit with what they can give you. Try to see their lesson through.

My advice is, don’t focus on finding the man you can love, focus on finding the next man you can learn from.

Be brave enough to look at who you are with and know why it makes sense that they would be in your life right now. Be brave enough to entertain the idea of having a man for whatever reason without feeling guilty about it.

The truth is, if you can articulate the reason that pursuing them makes sense for you, there’s no reason to be ashamed of having them in your world and there’s no reason to doubt yourself for making that choice either.

Just do yourself this favor: Don’t forget to pursue those dreams your ex encouraged you to neglect. It’s their turn now. It’s your turn. Sure, it isn't part of the Disney fairytale—not yet at least—but in today’s world especially there’s something wildly romantic about cozying up with your own dreams. There’s something intensely gratifying about being emboldened by your own ideals and not simply swept up by the promises that are made to you.

If I were you, I’d attend to the parts of myself that got overlooked or left behind in my last relationship and I’d distance myself from dating altogether, remembering full well that this singleton phase is just that—a phase in one long and winding and surprising life. Learn from it, don’t run from it. Then, after filling the sky back up with my own damn stars, I’d see whether the type of man I desire hadn’t changed significantly.

I think you’ll find that you’re more likely to be treated like a dream girl, if you’re already actively engaging your dreams.

Don’t neglect them. Not now. Not ever again.

Your dreams are one thing that no one should ever be able to take from you.

Guard them, honor them, and whether you’re with or without a man commit to your dreams without guilt.



PS: When I was single, I wrote an article about why no one should feel bad for me and, more importantly, why I didn’t feel bad for me. Maybe give it a read. Who knows, it could resonate with you.

A Breakup Coach trained and certified in Solution-Focused Life Coaching, Chelsea Leigh Trescott helps her clients turn their sob stories into silver lining breakups. Seeking advice? Send situation and question to for a chance to be featured.

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