The Last Day of Our Acquaintance

“You look good, -ish.”

This is going well.

I’m at a diner, one with an affinity for Cuban-influenced fare. We haven’t even placed drink orders yet, and she’s already cast her first stone. I look good. Ish.

It had been 15 years since my college girlfriend Sam and I last traded messages, and decades since we’d last seen each other in person. I still had a working email address for her when her mother passed away, so I reached out to offer my condolences. I had also recently welcomed my first child into the world. She already had two kids, so I thought she’d be happy for me. We were adults now, doing adult things. That’s how this is supposed to work, right?

But she never wrote back, so between that and her opening salvo here, it seems like a no. Cool.

“Um, thanks.”

“Be honest, is the hair real? I thought most of it would be gone by now.”

Plink. Another stone. Not a stone; a boulder. This is accelerating quickly.

“Yes. You think I would fake being this gray?”

“Whatever. When was the last time you spoke to Erin?”

Erin. She’s the reason the silence between us was broken. Erin is one of her sorority sisters, and one of my closest allies. She recently received a horrible cancer diagnosis. They gave her a 7% chance of survival. Fucking cancer.

Erin gave her my number and asked her to reach out to me, guilting her with some kind of sorority pinkie promise that, had she not invoked, Sam absolutely would have ignored. Whatever your thoughts may be about the Greek system, those rivers run deep.

“Four days ago. She wanted to know how the mixes were going.”


“She asked me to DJ her wake in the event that cancer wins.”

“Weird that you two are still so close. You should have drifted apart by now.”


“Huh. How are you?”

“Kim told me that you sent her a friend request, really? She hated you.” 


I knew this one was coming. Kim was her college bestie. Towards the end of our relationship, they were inseparable. I wasn’t a fan of hers, and she wasn’t a fan of mine, which made the Facebook thing even weirder.

On top of that, Kim told it backwards.

“She sent ME a friend request, which shocked me. I accepted it just to see what she was up to, but eventually, I realized that she wasn’t interested in being friends with me. She was just trying to promote some brand, so I unfriended her.”

“She told me you would say that.”

“Well, it’s the truth, so that might be why.”

Not the tone I wanted to take here, but she’s been throwing haymakers from the get-go. I had to draw a line in the sand.

It gets quiet for a bit, so I address the elephant in the room.

“I might be mistaken, but it feels like every one of your responses is designed to inflict the most damage possible.”

“Can you blame me?”

I can see why she thinks that.

She was my first love – and I hers – and I was completely unprepared for it, as most boys are. I was not taught how to talk about my feelings, so she never knew why I ended it. Hell, it took me several years to properly articulate to myself why I ended it, never mind anyone else, and especially never mind her.

The servers arrive. What timing.

“Hi there, my name is Sam, what can I get you to drink?”

Her name is also Sam. How about that.

She orders a tequila sunrise. She likes those? This is new to me, but then again, everything about her is new to me.

I order a Diet Coke and some water. Her reaction is one of utter betrayal.

“I’m drinking alone? Asshole. Are you sober now?”


“No, but seeing as you’ve already taken multiple shots at me in the first five minutes, it feels like keeping my wits about me is not the worst idea right now.”

“Again, do you blame me?”

“I’m glad you brought that back up. Yes, I do.”

Long pause. She clearly wasn’t prepared for that response.

“You’re kidding, right?”

“I know you’re surprised by this, and I totally get it. I never told you why I was breaking up with you – I just broke up with you. And let me just say that, on behalf of my younger, dumber self, I am genuinely sorry about that.

But no, I’m not kidding.”

Another, longer pause.

“Wait, are you saying that it’s my fault?”

“Let me guess, you’ve been telling yourself, and others, for all these years that I was scared, or I was broken, or that I was just afraid of being happy. Am I close?”

All the LOLs. So many LOLs.

“Yes, yes, yes. And worse.”

“I’ll grant you the first two. I was scared, and I was broken, and it would be another 10 years before I figured out why. So yes, scared and broken, guilty as charged.

But I wasn’t afraid of being happy. I just realized that I would never be happy with you. Would you like to guess why?”

“You are really laying this at my feet NOW?”

“Let the record reflect that you started this conversation topic, not me.”

“Worst chat ever. I want out.”

“Oh, no, we’re not getting this close to having a real conversation about this to not have a real conversation about this. What do you remember about things after we got back together?”

Yep, we split for a bit. It was torturous, for me, anyway. I was hopelessly lost. I listened to a lot of our favorite band, because you know, that’s a healthy thing to do.

But worst of all, in that small amount of time between breakup and reunion, I managed to break the heart of someone else who took a chance on me and was burned for their troubles. I regret that ten times more than what happened between me and Sam.

But I digress.

“I’ve tried not to think about it, really.”

“That’s fair. Would you like to know what I remember?”

“I haven’t gotten my drink yet, so no.”

“How about this: we wait until the drinks arrive. We can pick this back up then.”

“What are we supposed to talk about in the meantime?”

“Tell me about your life. How are you? How are the kids? Tell me something cool that you’ve done lately.”

“You realize that I don’t want you to know the answers to any of those questions, right?”

“Yes, but why? What’s the harm in telling me that you’re doing well, that you just did something cool? Living well is the best revenge, right?”


A really, really long silence.

I’m confused. I just gave her carte blanche to tell me how awesome her life is without me. I thought she’d run with that.


Holy shit. I’m such a dope.

“Unless…you’re not doing well, and something uncool just happened. Sam, are you okay?”

From the very beginning of the conversation, the signs were there; I just chose to filter all of her responses through her previous, post-breakup interactions with me. Not once did I consider that the reason that she was being hostile was because of outside forces. I made this exchange all about me, because in our previous email exchanges, it was. She always made it clear that she was still sore about how I ended things, and I carried that into this.


“Sam, seriously, are you okay?”

Sam the server arrives with drinks. Her timing is impeccable.

Finally, Sam the ex says something.

“Come on, let’s hear it. Go ahead and tell me what you have clearly been waiting for years to tell me.”

For the first time, I’m the one without a canned response. She’s exuded supreme confidence as long as I’ve known her. But now, she seems resigned, and it’s knocked me off balance.

So, I take a different path than I had planned.

“I wanted to tell you that I should have been a better boyfriend to you down the stretch, and I’m sorry that I wasn’t as emotionally available as you or I would have liked me to be.”

“Thank you for that. It’s way overdue, but I’m glad you have finally seen the many errors of your ways.”

I smile, “Cheers.” We clink glasses.

“Wow. This is a lot. How are you?”

“Shaken, but I think I will be all right, thanks.”

“What did you originally plan to say there instead of the apology?”

“I was going to tell her that I may have broken her heart, but she broke mine first. And then I was going to explain with painstaking detail exactly how she broke my heart.”

“You made the right choice.”

“Thank you, Erin.”

You probably have questions. We should go back to the beginning.

Sam agreed to talk to me, but meeting in person, or even a video chat, was out of the question. It would be text or nothing.

She didn’t even like the fact I had her phone number, but she needn’t have worried; I took the hint when she ghosted me after my son’s birth announcement. We would have this one chat, and I assured her that I would never initiate contact with her again. And I didn’t.

We each went to a place where no one in our regular lives would distract us. I went to the Cuban place, reading a book in between her texts (some of those gaps were lengthy). I have no idea where she went. Look at the chat again; outside of the tequila sunrise, she shared nothing about herself.

Well, except for one really, really big thing.

She asked me to send a photo, and I obliged. I sent a pic from a trip we had taken to Hawaii, so she could see my wife and kids as well. To be fair, it’s not the best picture of me ever taken, which might explain the ‘good-ish’ response. But we’re in our 50s, for fuck’s sake. We look good-ish on a great day. Every other day, we’d get thrown on the Bring Out Your Dead wagon.

She didn’t send me a photo in return. At the time, I chalked it up to her putting up a firewall when it came to me. Again, I filtered all of her responses through a ‘me’ prism, based on past experience.

But it wasn’t about me at all. She didn’t want anyone to see her.

I later learned that she had been diagnosed with Stage 4 pancreatic cancer several months earlier, and the subsequent chemo treatments were predictably awful. She was gaunt and frail, and understandably she didn’t want anyone who knew her in her prime to see her that way in the end. Once it was clear that the drugs weren’t working, she got her affairs in order and embraced a ‘ride off into the sunset’ mentality, hence the tequila sunrise.

“Unless…you’re not doing well, and something uncool just happened. Sam, are you okay?”

“Sam, seriously, are you okay?”

Twenty minutes passed between these two texts.

“Sam, seriously, are you okay?”

“Come on, let’s hear it. Go ahead and tell me what you have clearly been waiting for years to tell me.”

Three months passed between these two.

A month later, she was gone.

I have no idea if she read my final text to her, which I sent the day after her last one. I only know that someone read it. As for her ‘final final’ text, I’m guessing that was written by her daughter, because the tone was completely different than the other texts. Also, I received it the day after she died.

I was so ready to have that conversation, but not with a sick Sam. I was hoping for a happy, healthy Sam, one that couldn’t wait to tell me that no longer being with me was the best thing that ever happened to her. Instead, I was punching down without knowing it.

I also realized far too late that as much as she was attacking me, I was attacking her, too. My goal was to defend myself, and finally explain why I did what I did now that I knew how to put it into words. I wanted her to see the role she played in this, and that there was more to it than ‘I was young and stupid.’

Getting that text three months later changed everything. I still didn’t know what was going on with her, but clearly something was wrong. At that point, explaining my motive for ending a relationship decades after the fact felt meaningless, and really, it always was. It doesn’t matter why I did what I did – only that I did it. This whole exercise was pure ego massage, nothing more.

I do wish she had told me about her life, though. I really wanted to hear about all of the great things she did. Instead, there are about 50 people gathered at Kim’s house, telling tall tales about a life cut down too soon.

Meanwhile, I’m hundreds of miles away, in a bar with Erin. The glass clinking and the cheers earlier? That was her. Erin, incredibly, beat her cancer odds, and has a new ‘7%’ tattoo to document the win. I’m glad she’s here.

I show Erin the entire text thread for the first time. I wanted someone with perspective on the relationship to see how it went down at the very end.

“Wow. This is a lot. How are you?”

“Shaken, but I think I will be all right, thanks.”

“What did you originally plan to say there instead of the apology?”

“I was going to tell her that I may have broken her heart, but she broke mine first. And then I was going to explain with painstaking detail exactly how she broke my heart.”

“You made the right choice.”

“Thank you, Erin.”

“You knew this was a fool’s errand, right?”

“Of course I didn’t, because I’m a fool.”

“Nevertheless, he persisted.”

We clink glasses again.

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