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Learning how to let go in love.

I asked her, “you know what we’re gonna do?” and a small part of me felt like a manipulative piece of shit.

Because I knew that she was in an especially vulnerable place and that I could’ve suggested almost anything and it would have sounded like a good idea.

But it felt like the right thing to do.

And it also felt like the right thing to talk about, because she’d been holding on for far too long.

To somebody who hurt her in the worst way.

“We’re gonna delete the voicemails. All except one,” I said.

And I could feel the tension build and the emotions pile on and like the steam-engine of emotions was just building up momentum.

“I know, I know,” she said and I think she started to cry.

Letting go is hard and sometimes it’s impossible.

I started to get emotional, too.

Maybe through association.

I could hear the pain in her voice.

I was angry because I felt like this person had treated her like shit and she deserved better than that.

“Alright, are you ready?” I said.

As if we were taking a short trip to the mall.

But there was no going back from this.

“Okay, I did it,” she said.

All of the voicemails, gone.

And then all of the emotions came out, and both of us started to cry because this was hard.

Because we were going through something similar, in some ways and I felt her suffering.

“Thank you,” she said, in-between tears of joy and relief.

She said that she felt relieved.

Many of us are drawn to the pain of a broken relationship, and that’s what keeps us attached.

But on the opposite side of that — almost always — is liberation.

That can be just as empowering, sometimes.

We’re cheating ourselves.

A question that often pains me to get from my readers is almost always the question of, “somebody who I love is abusing me [mentally, physically] but I don’t want to leave them. What should I do?”

And I don’t have a good answer beyond, well, you should!

Because honestly, my experience in those sorts of relationships is approximately zero.

But I do understand enough about human nature to know that we’ll often continue to subject ourselves to those situations and those relationships because we enjoy the pain.

Not the soul-crushing defeat and the self-loathing that often comes with a broken relationship, but the void that that pain fills in our soul.

And that we won’t move on, more often than not, because the resistance to change is often far greater than the pain itself.

Because we need something to replace that pain.



Certainty that everything will be okay.

And if we don’t have that, we’ll never move on.

But we’re cheating ourselves.

We’re cheating people who we love if we don’t move on.

Love will always hurt.

The first time my ex and I acknowledged the fact that we were in love with each other was a strange moment.

“I have all of these feelings for you,” she said and I felt honored and humbled but I didn’t know how to respond.

“Are you falling in love with me?” I said, and she said, “that’s an unfair question,” and she wasn’t wrong, but now I didn’t really know how to recover from that.

And so, I told her that I felt similarly about her, too but I think she was worried that now, that moment, that was gone for forever.

That our Cinderella moment would never happen because I’d jumped the gun in a lot of ways or wasn’t able to fully express myself sooner.

And so, we were both disappointed in the outcome even though, at the end of it, was love.

I think that moment perfectly encapsulates just what love is: it’s inspiring, it’s confusing, it’s hard and sometimes it hurts.

When you’ve allowed somebody to get that close to you in your life, you’re basically giving them express permission to inflict hurt.

And you have to trust them not to.

I thought about that moment a lot, after we broke up.

What if I’d just told her, “I love you,” when I felt that way in New York?

Would she have told me, whoa, slow down there, we’ve only been together for a few months?

What if I’d lied, instead, and said, “I’m not sure how I feel about you?” And just perpetuated that lie and that disconnect through the length of our relationship.

Would that have been any better?

I doubt it.

Moving on from the hurt.

It never occurred to me to take the photo down until I was looking over somebody else’s shoulder in my bed and I thought to myself, would I want to see that in their room?!

Fuck no! I thought.

(And that’s not to say that tokens and mementos from past lovers aren’t healthy, important parts of life. Because they are. But if something were to trigger, ‘this guy has clearly not moved on’ more than an old photo, that might be the one.)

The answer wasn’t an urgent no but it was reassuring enough.

I kept looking back at the board, as we were rolling around in my bed.

“Uh, that’s a funny picture,” she said, and I had a momentary panic-attack.

Fuck! I thought.

I knew I should’ve put that away a long time ago.

Instead, she was pointing at the photo of my sister and I.

She pointed out that it felt uncomfortably close to the place where had sex/jerked off and I thought that was hilarious and also true.

I moved it farther away.

Close call, I thought.

Later that night, when she left, I walked over to my cork board, pulled the photo down, flipped it over and pinned it back in place.

The montage of photos replaced by blinding whiteness.

It felt like a half-measure, though.

Like I was still holding onto something by keeping the photo in plain sight.

The same with the letters: they were scattered among other letters from friends, family-members and loved ones but they were still there.

And all of the complicated emotions contained therein.

I asked my therapist if he thought that was normal — if keeping the photo intact, on the cork board and if keeping the letters on there, too, was normal.

If that was ‘healthy’.

He said, “yes,” and that an even healthier response would be to still hold onto those things, but to put them away.

To stuff them in a box, tucked under my bed.

So I did.

I took them off my wall, one-by-one.

I didn’t read them.

Maybe I will, in a few months.

I’m sure I will.

But I just put them away.

There was just one more thing I couldn’t let go of, though.


I was sifting through some of my most recent voicemails, and I saw one from my Uncle Mike who’d passed away in the last few months.

I listened to one of them.

“Hey, it’s your Uncle Mike — just calling you back. Call me when you get a chance. Love you, bye.”

I’ll keep those for as long as I can, and probably replay them every now and then.

I can’t remember where I read about people saving voice mails of loved ones who have passed away, but that article really resonated with me.

Text messages are, whatever.

But their voice?

It’s always great to have something to remember people by.

And then I saw a few from my ex.

I listened to them, too.

“Hey, I hope you’re spending some quality time with your family… was just hoping I could catch you before you went to bed…”

I miss her voice.

We haven’t talked in, I don’t think, a month or two.

I’m sure we will, at some point.

Whenever I feel “ready” or whatever the fuck that means.

Maybe not.

That hurts to think about.

I think about texting her all the time.

When I looked at those voicemails, I felt like a hypocrite.

Because though I’d encouraged my friend to delete her mementos, I couldn’t move myself to do the same.

So, I just stood there with my thumb hovering over the delete button.

What’s the harm of holding onto these? I thought.

(And the reality is, there is none. In fact, some people might argue that wanting to throw out everything from a past relationship is the unhealthy thing to do. The rash thing to do.)

So I just stood there with my thumb over the trigger, contemplating whether or not I actually could delete them.


And I thought about it some more.

I mean, I could just download these and save them on Google Drive, right?

And just hold onto them forever.

I moved my thumb over the ‘Delete’ button again, and this time I pressed it.

Then I scrolled down to ‘Deleted Voicemails’.

‘Clear All’ would erase all traces of them.

‘Permanently clear deleted voicemails?’

And then they were gone.

The rest of the memories tucked away under my mattress.

I’m sure I’ll revisit them, one of these days.

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