Dating Your Ex, The Best Or Worst Idea You’ve Ever Had?


Sometimes we have to learn a lesson twice. We forget to read the fine print. There is reason the cliché exists: fool me once shame on you, fool me twice shame on me.

Sometimes, in the cold of winter, on a long drive, or at dinner downtown with a well-made Manhattan in hand I could completely forget what had happened. I could forget the sleepless nights or the anxiety in the grocery store. I could forget running back to California to lick my wounds. I neglected all those things I swore I would never forget again. All of this because I went back. All of this because I was dating my ex.

I can talk about this now because the vantage point feels high enough. I was too close to the blast radius before. I couldn’t be helpful or honest about why we do the things we do. I’d like to preface this whole conversation with the fact that I wouldn’t change a single moment.

The truth is, the second time around was far less painful and way more instructional. And now that I’ve climbed out, limb by limb, I can examine the things I found in my no-man’s land. Most of them are simply questions to consider when you sit down at your table. You need to take stock in what you’ve got and keep tabs on what you want. So, ask yourself…


Is there still poison in the cup? And what I mean is, is the reason you split last time still on your lips? It doesn’t have to be a hulking reason, because a slow bleed is just as deadly. But I’ll tell you my truth: if a separation didn’t drag it up from the depths, then nothing will. Either call it out or call it quits.

Do you truly want to be with this person, or do you happen to be with this person? It’s no secret we often confuse comfort for something other than what it is. But just because you know where they keep their water glasses in the dead of night doesn’t mean you should be there.

Can sex with an ex ever just be sex? You tell your friends, oh we’re just sleeping together. Sometime you even mean it, even believe it. I don’t know though. I am not sold on the idea that you can fuck someone who you once loved and not in someway spinal tap into those feelings. How do you surgically remove that part of a relationship? You don’t.

And in my opinion the most vital piece of advice I’ve brought back to the surface: speak up. If you cannot say what you want or need for fear of (fill in the blank) then you are in the wrong place, or at the very least, the wrong time. You owe the both of you lip service to the situation. Because at the end of the day there are still two people in that bed.

None of this negates the absolute necessity in learning your lessons to the bitter end. I don’t think I ever would have truly left if I hadn’t gone back, and I cannot punish myself for it. I’ve become a really firm believer in the idea that a lesson will teach you how to learn it if you hang in there with it. And that nothing is over until it’s really truly fucking over.

A Midweek Meditation on Zadie Smith’s Literary Brilliance, Michelle Obama’s Grace and Common’s Never-ending Creativity

This week, I’m leaning into love. Love for literature and one of its most brilliant minds. Love for our First Lady who feels like family instead of political royalty. Love for Common, a man whose trademark creative impulse shines on an unofficial remix of “Cranes in the Sky.”

View Article

Beauty Essentials…