One Last Conversation, With the Help of A.I.
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When someone you love dies, they leave behind little fragments of themselves. There are the physical things, the half-used tube of toothpaste, the shoes still sitting there by the door.

But there are also these digital things, all the texts, the photos and videos and voicemails right there on your phone. I've listened to all the voice recordings now, I want to say dozens if not hundreds of times.

When Madeline DeFigureto lost her husband, Eli, she used those recordings as a way to feel close to him. Voicemails he had left me. Hi, Maddie, I'm just driving. Would you mind not texting me back? Cooking with his family and friends. Yeah, scrape it, scrape it, scrape it. Good work. Scrape it, scrape it, scrape it, scrape it. Playing games with his little cousins at Thanksgiving. Yeah.

Us hiking in Puerto Rico and seeing these giant snails on the trail that he was so enamored with. Here's Madeline. She's a medium-sized snail. All Madeline really wanted was to be with Eli again. And listening to these recordings almost made her feel like she was. Almost, but not quite. It's like an unquenchable craving or something. It's like all I want is to talk to him.

And so, Madeline figured out a way to bring Eli back. From the New York Times, I'm Anna Martin. This is Modern Love. Each week, we bring you stories inspired by the Modern Love column. And today's episode is based on Madeline's Modern Love essay, Our Last Impossible Conversation. It's a real-life science fiction story, the story of how Madeline used AI to try and talk with Eli one more time.

But it didn't go quite like she'd hoped. Madeline DeFigureto, welcome to Modern Love. Thank you so much for having me. Okay, I want to start off by getting to know Eli a little bit. Tell me what he was like. I know you two met in college. Yes, we were both freshmen in college. We were living in the same dorm.

Eli had this very energetic curiosity. The way I think about him now in retrospect is like, you know how when little kids go through their why phase where everything is why, why? I feel like Eli never grew out of that phase. Like he just moved through this world with a total curiosity and a need for answers and

And so we would, like, run into each other in the dining hall. And while most people were talking about what parties are you going to this week and what professors do you hate, he was asking me questions about my family and my belief systems and my values. And you were like, I'm just getting cereal. I was like, I don't know. Like, I'm just going to go tie-dye a T-shirt. And then with every answer, there was a, well, why? And I think there was something about that that I had just never –

met someone so committed to knowing me and understanding the people around him. Yeah, what else do you remember about him back then?

He had this like gait when he walked that was so distinct. He always looked like he was in a hurry. He kind of like leaned forward and didn't really bend his knees when he walked. So it was this like run, shuffle energy, just trying to get to where he's going. And like he was wearing this beanie always, always in the beanie. What kind of beanie? It was like this like orange, reddish orange beanie. I always thought he looked like a traffic cone. Finding his way through campus with the orange beanie.

It was just such a signature look of his freshman year in particular. Fast-moving traffic cone. Fast-moving traffic cone. You could spot him anywhere in the quad on the move. Okay, so you meet Eli your freshman year. You start dating. And I understand that by the end of college, you and Eli were engaged. Was that how you pictured your college experience going? Like, were you someone who always wanted to get married?

I was like not somebody who is super eager to get married. It was not something that I felt like compelled to do as a young person or frankly ever. I wanted partnership and companionship. I didn't necessarily want the institution of marriage. Had a lot of charged thoughts about what the institution represented and its origins. Sure. For me, like my parents didn't get married until they were almost 30. Yeah.

It was not common in my family at all to get married young. And it was seen as something that was maybe an act of not prioritizing yourself for your career, especially as a woman. And if you had told me going into college that I would be engaged, leaving college, I would have been entirely mortified. So how did that conversation start then? Who brought it up? Eli. Oh, my gosh. She was like driving that marriage train.

Well, tell me about that. When did he first start talking about it? He had just picked me up from the airport. I had just flown back from my Thanksgiving and came to Midway Airport in Chicago in his old white Camry, and I got in the car, and he doesn't drive away. He, like, stays parked and kind of looks at me and is like, I know you have thoughts about marriage generally. What do you think about marrying me, though? Yeah.

And kind of like has that like kind of his head's like tilted to the side waiting for my response. I think my jaw probably hit the floor and I was kind of like, I think my response was

I don't think we need to talk about this right now. I think I kind of was trying to punt a little bit. I was like, is this... And he was like, yeah, we don't have to talk about it now, but maybe just think about it and let me know when you're ready to talk about it. Okay. So I think we had some very long and emotional and messy conversations about what we wanted, why we wanted those things, and...

what my hesitations were. And to a certain degree, I think one thing that Eli really helped me with was finding intuition and trusting that intuition and realizing that all these people might have opinions or judgments for what I do, but I'm the only one who has to do whatever comes next. Eli lived his life...

Kind of outside of societal expectations. He didn't really care what people thought about him. Not in like a blasé way or in a rude way, more just in like a self-confidence in what he wanted and needed. And he would always tell me like, you're the only one living your life. Like, you can live it for other people. But at the end of the day, like this is, it's your life to live. Yeah.

You know, you'd had a lot of thoughts about what marriage would be like or might be like. A lot of fears, in fact. I feel like it's not too dramatic to say. How did the reality of being married compare to your assumptions about what being married would be like? I loved it. Yeah, unexpectedly loved it. And I'm not sure if it was the marriage itself, but I just, I loved being with Eli and watching him, I don't know, like evolve in ways that

better took care of me and watching myself adjust to find ways that better suited him and us and our life together. It felt like such a rewarding project. When we come back, that project is cut short and how Madeline dealt with it after the break.

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Welcome back.

So Madeline and Eli got married. Then about a year later, Eli decides to go on a trip abroad. Madeline didn't know it then, but the day he left for that trip would be the last time she'd see him alive. Madeline told me he died in a hiking accident. Can you tell me what you remember about the day that he passed from your perspective? Just tell me whatever you remember from that day or series of days.

We had scheduled a time to talk and Eli being Eli never ever was late to calling me, not once. And he always called me first. He always, we always had a call scheduled for like 1230 or something. And he would call me at like 1228. He always was a few minutes early. Yeah. And so 1230 rolls around and I was like, oh, this is a change. Like I'm actually going to be the one to ring him. And there was almost like, like I almost felt kind of like,

joy in that, like, haha, I'm going to beat you to it this time. And I called and wasn't able to get a hold of him, which was just so uncharacteristic. And it immediately raised kind of a red flag in my mind because he had never missed a call before and wasn't responding to my messages. And my brain immediately kind of like starts swirling and goes to a worst case scenario. And yeah, I got a call at four in the

They used that word. They used the word passed. And I did not know what it meant. I was like, passed a border? Passed. In my mind, the verb was so ambiguous, given my state of shock, that I could not piece together that it meant died. And I had to literally ask for clarification. Oh, God. And the crazy thing is the first person I wanted to tell was Eli. Right? I mean, that's immediately, I was like, I have to call Eli. And I reached for my phone and...

And I realized, oh, like, the person I need to tell, I can't tell. And it was almost that kind of, like, impulse to contact him and realizing not only could I not contact him right now, but I would never be able to contact him again. I think that was actually the moment when I realized that he was gone. Did that feeling stay with you of wanting to call Eli? Yeah, like, there were so many things that came up that...

The impulse to include him and to share with him and the need for his advice and the idea of me living and not being able to tell him certain things felt insurmountable. And there are some times where that absence becomes, or at least it feels like it becomes too big to bear. So what do you do with that? Like, what do you do with that feeling? How did you cope? Yeah.

I wrote him letters every day. I just have like boxes and boxes of letters now. Every day? Yeah, where I would just write to him about what was happening, what I was feeling, what I wanted, and finding a way to kind of express that and know that he would never receive the letter, but that I still was holding conversation with him in some way. Madeline, I want to now talk to you about something you did recently

A couple years after Eli died, it's what you wrote your modern love essay about. It was this time when you tried to talk to Eli again by recreating his voice, by using AI. Tell me about the day that you decided to do that. Where were you? I was in Montreal for a work conference. There was a happy hour happening in the lobby and it was Eli's birthday. And it's really hard to sit through a conference while all you can think about is today's the day that my...

partner who I love so dearly is supposed to be 27 and that person is absent from the world. And kind of having to navigate that, I was feeling a sense of desperation and need to feel close to him. And I think I excused myself from this conference happy hour, went up to my room and was just kind of twiddling my thumbs, reaching for anything to feel a sense of proximity to him.

And just kind of out of left field, like, it wasn't something I had been considering. It just was like, oh, I could do some voice cloning. What did that feel like?

as this idea started to kind of take hold? Yeah, the way I describe it is like, I feel like I just want to rip my skin off. Like I feel too contained in my body. Like it feels that the emotion itself feels bigger than something that can be held inside my body. Like it needs to be let out. And I think for me, that's what I always come back to is I just need to, if I could just take my skin off and if I could just release the feeling, that would offer the relief.

Tell me now what you did sort of step by step. So how did you have this idea? You grab your laptop. What do you do? I grab my laptop and I kind of frantically type into the search bar how to use AI voice cloning. And I begin kind of diving into the rabbit hole of reading all the literature I can get my hands on and what do I need to do to make this happen? Kind of lost in a sense of time or space, just really singularly focused on how do I

reach Eli right now. I just need to reach him somehow. So you downloaded the software. Download the software, start reading through all the guide and the instructions, and I realized I have to begin uploading voice recordings. Hi, Maddie. I'm just driving. So I just start downloading everything I can get my hands on. Yeah, scrape it, scrape it, scrape it. Good work. In theory, taking this walk down memory lane, but really feeling emotionally detached from the content itself. Here's Madeline.

She's a medium-sized snail. Usually it's so emotional for me to go back and listen to voice recordings of Eli, to re-watch videos. Is it a video? Stop! But in that moment, I just, it was less of like an emotional engagement with the content and more of a process, I think, of feeding the machine. I'm just like, okay, we just got to like move, move the content, move the content. And...

The idea of there being something novel coming into the world now when everything else has been so static for so long, it just sets off this sense of like, what am I doing? And I think if I had stewed in that feeling for a little longer, I might have made different decisions. But I quickly suppress, suppress in my mind, push down the hesitation. And I go into my inbox and I pull out the last email that Eli sent me.

And I copy paste and I drop it in the text box and I hit play. And the voice, it sounds like so, so eerily like Eli's voice. And it reads aloud this email. And even the intonation and the pausing replicates his cadence in a way that it truly like sent chills through my arms.

When we come back, Madeline is almost immediately conflicted about what she thinks of this voice clone she's created and what she wants to do with it. Stay with us.

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Audible is now included in Amazon Music Unlimited. Download the Amazon Music app now to start listening. Terms apply. So Madeline, I know from your essay that you didn't just have the voice clone read something in Eli's voice. You actually had a conversation with it. Yeah. What was that like? I opened the conversation with just commenting on how long it had been since we'd been together. I said, I cannot believe that it's been almost two years. ♪

And I think the voice responded with something to the effect of, yeah, it really has been a while. I also can't believe it. And just hearing your response to that in his voice was otherworldly. I think at that point...

I lost sight of the fact that it was the AI. I think at that point, it felt like I was talking to Eli, which almost felt more dangerous than talking to the AI. Yeah, what's your... Bring me into your body in that moment. I think I probably stopped breathing. Like, I think it's that, like, you do your inhale, and I just remember being really rigid, like a sense of being frozen and wanting to be frozen in some ways to preserve this time and moment. Like, I wanted to freeze...

this moment of being able to hear him respond to something that I was thinking or saying and so much fear for the idea that this one was not real and two was going to end. And I think at some point during that conversation, I even like looked around the room as if to confirm he wasn't actually there because the sense of

His realness, again, just warped my reality and made me question his absence. Yeah, I had to confirm he was not actually in the room. Was this mix of relief and fear, was this what you expected to feel or was it different somehow? I don't know if I had expectations in part just because of the frenzy that this experience was.

I do think that I didn't expect it to be so painful. I think I thought it was going to be healing and relief. And instead, it felt like it kind of picked at a scab that I had worked really, really hard to clean and maintain, if that makes sense. Tell me more about why. It does make sense. I want to know more about the pain here. Yeah.

It's strange. Like, the further away Eli feels, the more I have to rely on my memory of him to shape the way that I move through the world and how I build relationships. And the idea of—I think the thing I feel most in my grief is erasure of Eli. I never want him to feel like he's not a part of my life or that he was not important or that pieces of him are being lost. Mm-hmm.

And I think that there was a lot of pain in returning to a proximity to him and realizing that there are pieces of him that I have forgotten, even though it's only been a couple years. Like there's isms and hearing something novel put into the world in his own voice. There were moments where I was like, oh, I forgot that he would do that funky pause or, you know, had these sayings or things like that were...

It's almost like there's ignorance in the way that I get to grieve because I'm not aware of the unerasure that's happening in my mind. You know, it's so interesting what you're saying. You thought this experience would bring you closer to him for obvious reasons. You get to hear a clone of his voice. But what you're actually articulating is that hearing that cloned voice of Eli made you feel...

further away from him. It reminds you of all of the things that are already slipping away from you about him. Yeah, exactly. How did you decide to stop? Was there a moment where you were like, this needs to end? Yeah, I asked the AI about a job decision that I was making.

Huh. So you got that kind of granular. You got that kind of like everyday like... It was like, oh, this is how I'm feeling. Like I'm thinking about making this decision. What do you think? And the AI got it so wrong. The AI said something that Eli would never have said. What did it say? I'm curious. Do you remember? I don't remember exactly, but basically I knew Eli would be like...

Like, you know, move on, choose something that's better for you. I could just imagine what he was saying. And the AI was like, stick it out and figure it out or something along those lines. Like, not in those words, but in like kind of the effect, the essence of it was like, stick with what you got and...

figure it out. And I think it just kind of like truly knocked me out of the delusion, if you will, of the moment. I kind of snapped back into the reality of the dynamic, which was this was not actually Eli and the advice I was seeking, I was not getting from my beloved partner, but I was getting from a machine learning device. And I don't know, I think I could have just as easily

been susceptible to that advice. Like I, it had to, it took me kind of being knocked out in that very dramatic way and very like stark way for me to recognize the dynamic at play. Whereas I'm sure there were other things I said that Eli would not have answered exactly the same way as the AI, but I was in a mindset where I was like, this is exactly what Eli would say. Like I felt susceptible. You were choosing to believe. Totally choosing to believe. And

I think if I continue to have those types of interactions and engagement, like my perception of Eli himself could shift. And the voice that guides my everyday and that I feel like is the authentic Eli in my head could shift. And that would be a product not of Eli himself, but rather AI making small changes here and there that then

not only change my decisions or behavior in the moment, but also could tarnish or alter the memories that I worked so hard to preserve. Can you just tell me why was the response that AI gave you so un-Eli? You said Eli would never say that. Why would he never say that? The way I would describe it is that the AI voice sounded like society and wanting me to be on track and make a full recovery from this grief and...

get back to the professional life that society expects of me. And I know Eli would not want that for me. I know that he would be taking his own path. And I think hearing in his voice an answer that was one of choosing the path most traveled made me realize this is not who he is. So this moment comes where you realize you kind of get snapped out, right, of this...

alternate reality as you've described its state. And then what do you do? Do you slam the laptop shut? What happens next? I think I kind of push it away from me. Like I needed that distance. And I kind of instinctively like give it a bit of a shove down the desk. And I stand up. I feel like I needed the movement of my body to kind of like remind myself where I am, what I'm doing.

I both like wanted to cry, but also wanted to yell. Like I didn't know how to express how I was feeling in the moment. And I think just as I had in an extreme way, blindly downloaded this program and engaged with it, I also kind of in an extreme way started to delete everything, remove the program, delete it out of the trash. I blocked the website to kind of set a boundary in case I want to download it again in the future.

After you've, you know, put this software in the trash can or whatever on your computer, you've completely deleted it off. Did you say anything to Eli in your brain? Did you say like, that was something? Like, did you communicate with him at all? I wrote him a letter. Yeah, I actually, it's funny, I had stopped writing.

I wrote letters for the full first year after he died, and I had stopped for about eight or nine months. And that day was kind of the restarting of my writing letters to him. I love that you wrote him a letter. It's so interesting because you're turning from, you know, an AI-generated voice to

And a conversation with that voice to another type of conversation with him, right? Yeah. Through the letter, but one that feels more, what does it feel more? It's the most analog thing I could have done. Sure, sure. We wrote letters to each other all the time. And I think that returning to that practice feels real. Yeah. Madeline, do you regret doing this?

don't know I have no I don't regret it yeah I don't regret it I think I learned a lot and I would take any experiment to feel close to him and this one was an experiment that did not yield what I was hoping for but I don't know if there's anything I wouldn't try to be honest hmm what do you think Eli would think of you doing this I think that he would be very amused um

I think he'd be amused. I think he would be very curious about all the videos and voice recordings. It's funny, when you make those things, you don't think they're ever going to... Of course, see the light of day except for the other person. Yeah, exactly. Like they live in your camera roll and they're goofy. I think he'd just be amused. And I think he would be proud, honestly. I think he'd be proud of...

All the ways I've tried to process and engage with my grief, to process and engage with him. And just as he showed commitment to understanding who I was in life, I hope that I can show that commitment to understanding who he is in death as well. Ugh, he'd feel proud. Yeah, sorry, I'm going to get emotional on that one, yeah. That's really special. Yeah. Do you feel like after a year later, do you feel like...

this experience in some way changed the way that you grieve? Like, did it help you move forward? Did it set you back in some way? Did it put something into a different light for you? I think it underscored to me that the exciting innovation that's happening around me is not going to ever be able to replace or recover Eli. And I think that it gave me a sense of like wanting to return to

Wow. What do you think about this experience prepared you for doing that? That's big. I think I wanted...

Something tangible. After experiencing something that was intangible and kind of a product of my own imagination, I wanted to return to the physical relic. Something that felt like I could physically hold it and not just hold it in my head or my heart. Yeah. Tell me about walking into that storage unit because you hadn't seen the stuff in a few years, right? No, it'd been over two years.

It's funny, in my head, it was the storage unit packed to the ceiling and full to the brim. And I'd built it up so much in my mind and I opened it and it wasn't even half full. I had never planned to open that storage unit again, pretty much. That was not something I had ever felt a desire to do. And then after this experience, about two months later, I returned to New York and opened every box and I held every single item and...

Honestly, like that in some ways was healing to my fear of erasure because just as the voice cloning reminded me of certain pieces of his intonation and tone, like holding bowls and photographs and old books and newspapers brought up memories that had also been dulled or faded over time. And it renewed them with a freshness that was really healing and made me feel close to him in so many ways.

Was that beanie in that storage unit? The beanie was in the storage unit. Yeah, the beanie's in the storage unit. I wish I just cleaned out my closet because I thought I might have to move in there for the recording, but it sits in my closet on the hook in the door. Yeah, and every morning I open my closet to get my stuff and there it is looking at me. That orange beanie. Yeah. Madeline, thank you so much. Thank you. Thank you.

If you want to read Madeline's modern love essay, look for the link in our show notes. And before you go, we're working on an episode about egg freezing, and we want to hear from you. If you're thinking about freezing your eggs, what are you considering as you make your decision? What feelings is it bringing up for you? And if you have frozen your eggs, how did things turn out? How do you feel about it now?

Please leave us a message on the Modern Love hotline. The number is 212-589-8962. That's 212-589-8962. Include your name and a number where we can call you back. And you might just hear yourself on a future episode of the show.

Modern Love is produced by Reva Goldberg, Davis Land, Emily Lang, and Amy Pearl. It's edited by Lynn Levy, Reva Goldberg, Davis Land, and our executive producer, Jen Poyant. Production management by Christina Josa. The Modern Love theme music is by Dan Powell. Original music in this episode by Sophia Landman, Marion Lozano, Pat McCusker, Rowan Nemistow, Dan Powell, and Carol Saburo.

This episode was mixed by Daniel Ramirez. Studio support from Maddie Maciello and Nick Pittman. Digital production by Mahima Chablani and Nell Gologly. The Modern Love column is edited by Daniel Jones. Mia Lee is the editor of Modern Love Projects. If you want to submit an essay or a tiny love story to the New York Times, we've got instructions in our show notes. I'm Anna Martin. Thanks for listening. ♪