The not so subtle art of dating an ex.

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“Do you seriously want me to answer that question…?” my good friend asked me from across the table.

I nodded.

A few hours before I’d been sitting at the bar with him, I was hanging out with my ex-girlfriend who had broken up with me days before that.

“Yes, you’re delusional,” my friend said and I nodded again but I felt this weird zen-like serenity inoculate me from that reality.

I was sad about the breakup. Depressed, even.

But I’d convinced myself that I could navigate those complicated emotions without space.

That feeling wouldn’t last.

He suggested I take a few weeks off of seeing anyone.

That sounded like a good idea but not something in my current state that I ever felt like entertaining.

So I saw her the next day.

And the next few weeks.

Months, even.

Follow the leader.

A few days later, we’re at lunch and she asks, “In this dynamic, can I kiss you, or…?”

And I said yes because my immediate response to her was that I ALWAYS WANT YOU TO KISS ME. ALWAYS. 

And still, neither of us would feel obligated or particularly compelled to call during the week.

Not like we used to.

But conversations led to meetings, meetings led to reconnections.

Reconnections led to sex.

I loved those parts.

Side-note: this article is part of a 5-day series on dealing with heartbreak, jealousy and suffering in relationships. Click here to get immediate access to that series.

I’m a romantic at heart. Or I’ve deluded myself into believing that I am.

(Kissing is my favorite. Sex is a close second.)

So, we started doing what amounted to casual dating.

Hanging out. Having fun. Getting together. Drinking wine and eating sushi together. Casual companions.

And for the most part, it felt amazing.

Minimal investment.

That it’ll be a fun thing for a while and we’ll date and we’ll fuck and then we’ll go.

Fewer expectations lead to less disappointment, right?

The arrangement.

“Let’s keep this casual,” she said and I agreed.

And she asked, “do you feel okay with this?” and I said yes, because the honest answer is that up until recently I was.

I wanted to delay what I felt was the inevitability of a flameout.

Like what had happened when we first started dating.

Hot and cold.

I wanted it to be hot. Or, at least warmer. 


Not something I spent a lot of time or energy or anxiety or frustration thinking about.

And that’s how it had been.

It felt like a torrid affair: something we’d go about in secret, behind someone’s back. Even though we never hid it.

We’d schedule casual dates, but not as often as we used to.

More: what are you up to on Thursday? 

Okay, cool. 

And then we’d hang out.

It was fun, and then it would end and afterward the question that would almost always linger is: what do I want out of this? 

For a while, I had no fucking idea so I just kept at it.

And then recently I stumbled upon the answer.

More than this, I thought.

Acting when it feels right.

Months ago, a few days after we first “broke up”, I called her and told her I needed more time.

A few weeks, I told her. Minimal communication. 

I felt so conflicted with that decision that I reneged at the end of the phone call and admitted, “I think we should still be friends…”

It felt like we’d been playing emotional chess and she was a grandmaster and I’d lost my queen on the second fucking turn. 

Within about two or three weeks, we were spending time together, hooking up.

Because I missed her so, so much and I was still in love with her and I still am.

The next time around, a few months later, when I came to that decision again, it felt different.

I was sitting down with a cup of coffee, journaling at a coffee shop, reflecting on jealousy.

Jealous because she’d told me the day before that she’d hooked up with somebody during the week and even in spite of the fact that we weren’t really together, it still hurt.

(And sidenote: it was an open, polyamorous relationship, and I would’ve been a total hypocrite for not accepting it seeing as I’d done the same thing a handful of times while we were dating.)

Jealousy is a bitch. (More on that in another article, some day.)

And so I wrote down my thoughts on insecurity, jealousy, envy, rage, everything that I felt.

I came to the conclusion that I didn’t care about the hookup. Not anymore. That I was letting something stupid and completely unrelated dominate my emotions and that I should just let it go.

In fact, I was happy for her. I loved her more for sharing that with me and I wanted her to know it didn’t matter to me even if I was bad at communicating that.

And that, in a healthy polyamorous relationship, I’d want that for her (especially if it made her happy).

(And that’s a real thing in the world of polyamory, and it’s called compersion. In theory, it’s amazing. In reality? Difficult to practice. It requires serious emotional maturity, trust, and self-esteem that I haven’t yet found in myself.

But we weren’t in a relationship.

We were in that weird, emotional middle. The one between a loving relationship and a fuck-buddies kinda scenario.

And it worked for a while. And I was happy. I was cool existing in that proverbial gray.

Then, as I was writing my thoughts out on paper, my hood over my head to protect my emotions, I got the clarity I wanted: I don’t need this anymore.

That I was relying on it to fill some sort of emotional void in my life and that felt wrong and unfair to both parties.I wasn’t happy with it and I was lying to myself and her.

And I had to accept that I could, in fact, love someone to death and not want to be with them anymore.

I just stared off into the distance and let that reality sink in.

I smirked because clarity is a powerful feeling.

(Especially when you’ve felt so unclear for so long.)

Moments later, I got up, tossed my coffee in the trash, hopped on my bike and left with a sharper sense of my new reality and stronger conviction than I’d felt in forever.

Like I’d finally gotten permission from the universe to move on.