I Love You, Now Die director interview: ‘There are so many questions that continue to haunt me’

The director of true crime documentary I Love You, Now Die talks, ethics, justice and our changing relationship with technology

True crime documentaries have never been more popular and now Sky has launched an entire channel dedicated to the genre. One of the first docs to appear on Sky Crime is I Love You, Now Die: The Commonwealth V. Michelle Carter, a fascinating look into a particularly bizarre and tragic case, that of Michelle Carter and Conrad Roy.

The pair were teenage boyfriend and girlfriend who conducted the majority of their relationship via text message – they’d only met in person a handful of times. Both had suffered from mental health problems and in a terrible tragic twist, in 2014 Conrad took his own life. But it transpired in the run-up to his death, Carter had sent a series of text messages which seemed to be coercing Roy into going through with it.

Can a person be prosecuted for committing a crime when they weren’t actually present? Is Michelle culpable for Roy’s death, even though he’d had suicidal thoughts in the past? What’s the legal precedent for a case like this?

It’s a complicated case with multiple layers and nuances and the documentary, split into the case for the prosecution, and the case for the defence, attempts to present both sides as fairly and sensitively as possible.

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The director of the show is Erin Lee Carr, a documentarian known for docs Thought Crimes: The Case Of The Cannibal Cop and Mommy Dead And Dearest.

Den Of Geek sat down with Lee Carr to talk through the details of the case, the experience of documenting something so emotionally charged and the public’s fascination with true crime cases.

Warning: this interview is extremely spoilerish, in depth and long – if you haven’t seen the documentary, which is available now on Now TV, then you should check that out first. The interview, and the doc also deals with difficult themes, if you have been affected by any of these issues there are some links at the bottom you might find useful.

When did you first hear of this case and why did you think this would be a really good subject for a documentary?

I have forever been fascinated about human beings and our relationship with technology, and the good, the bad and the ugly that can happen over the course of thinking about it. And so, when I heard there was a Washington Post article that had a Michelle Carter text message – I think it was “It’s now or never” – in my mind it really was like, there’s such a greater story here. I mean, nobody says those things without reason, it felt very confusing. So I really wanted to use my time on earth to be a part of investigating that.

I first heard about it on a podcast but after watching your documentary I felt quite differently about the case. I wondered if you started with preconceptions about the case and whether they changed as you were making the doc?

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I was pretty horrified with the text messages. I mean, we all think about on our worst day – you Rosie, me, Erin, looking into our phone, you’re probably not saying things like that. We’re not getting even close to saying things like that. And so it was like, is this woman a psychopath? Is she a sociopath? Is she someone who is mentally very troubled? Was this fabricated in some way? So there were all these things that were floating around in the ether, trying to understand what it was and the portrait that emerged is really of two troubled, sick teenagers. I think that we like to think of our killers of having black moustaches and carrying daggers. And what I find is evil comes in many forms. And I don’t think Michelle is evil. I just think that this was just such a chaotic, incredibly scary time for both of them.

You obviously had to be very selective about what you included from the court case. Was there much that happened in court that you were upset to lose?

No, I personally wish that it had been a jury trial, I think that it would have been a lot longer if it was a jury trial. They ended up doing something in the US called the bench trial, which means a judge determined her fate. I was really trying to wonder and figure out whether a jury of Michelle’s peers would have found her guilty or not guilty, but ultimately we will never know that. And so I think, for me, it was using the film to create a portrait and a case study so that we, the audience, are her jurors and how we feel about her once we see the mitigating evidence.

The crux of the case was the call where Michelle supposedly told Conrad to get back in the car but of course there’s no record of that. Was there much more about the content of that call what was discussed in court?

No. Literally there’s no record and it was two phone calls, I believe one was 47 minutes, one was 49 minutes so it was over an hour long and there’s there’s no evidence, ever, that told us what was inside that phone call. Michelle Carter never took part in her own defence, never took the stand. And so it has very much remained a mystery what exactly happened over the course of that phone call. But we what we do know is that Conrad died. At the end of that phone call he was no longer living on this earth. So I think we can begin to examine what might have been said.

Do you have a sense of why Michelle didn’t take the stand and did her lawyers talk about that?

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So, it’s really interesting as a crime filmmaker, I have yet to see people take their own their own stand in their defence. I think you do it if you are in the worst possible condition, because during cross-examination a prosecutor can basically really in a deliberate and debilitating way, ruin your case so people so rarely do it. Defence lawyers rarely advocate for it. I am hoping to someday work on something where somebody takes a stand in their own defence, but I have yet to see it. It’s not like in the movies, you know?

So she presumably never specifically said that she didn’t say to him “Get back in the car”?

Yeah, I mean, it’s a good question. I don’t know if she said that. I guess I cannot confidently say either way that she said to do that. I think if you’re somebody who studies the case, long term, there’s a lot of fabrication inside the text messages. Not even just to Conrad but to her friends. Like, she would say, ‘I’m doing this’ and she wouldn’t be doing it. And so for me, there’s always been an area and an element of deception related to the text messages. So I’ve never really been able to really truthfully take them at face value.

This is so fascinating because of the legal precedent. I wondered if there has been anything similar that has gone before?

Yeah, I studied a criminal case and in Minnesota where a guy online was trying to get people to kill themselves. There’s been cases that have appeared since Michelle Carter’s conviction. I think that this is singularly unique in that you can argue it either way in that he was intent on committing suicide and he did it, or that Michelle Carter really drove him to that point. There are just so many questions that continue to haunt me and continue to haunt every single person that knew them. Because it’s not about me as a filmmaker and what I think and what audiences think, it’s really about the healing of Conrad’s family. And I think that because of all the speculation I imagine it’s so much more difficult for them to heal

Do you think she was treated differently because of her femaleness? I read a review that used the phrase: “Massachusetts has its own history of attributing sinister powers to teenagers” (referring to the Salem Witch Trials) – what do you think?

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I think that yeah, these places leave imprints and the fact that the Salem Witch trials took place there, that tended to vilify women in these roles – I mean, I just think that as far as we have come as a community in terms of our legal precedent, I think that there is so much confusion about guilt versus innocence, about time served. I think that the criminal justice system is pretty archaic and, and deeply punitive. And so I think that there’s just there’s so much going on there that the defendant can’t control.

You also made Thought Crimes: The Case Of The Cannibal Cop which is also very interesting in terms of legal precedent and when imagining, and talking about doing something can count as criminal. Is that something you’re particularly interested in, these odd, on the edge cases?

Oh you know it!

I am forever fascinated with the legal system and technology. I truly wish I had legal background in order to – like sometimes when I’m trying to read all this court paperwork, and I have to ask my friend who’s a lawyer – so part of me really wishes I had more of a background in it. There’s such a huge audience for true crime and for psychological thrillers and that’s personally what I like to watch and think about. I think it’s less about the elements of the crime, but really about all the days that lead up to the crime. And I think that that’s where we’re at in terms of a community, engaging with the material and seeing every single person as a human being. And I think that’s, that’s difficult.

Obviously empathy and ethics are really important as a documentarian and you made sure Conrad and his family were the focus – how difficult a terrain was that for you to negotiate?

I remember being at the courthouse and you really are surrounded by a lot of press and a lot of people trying to report on a criminal case, but the family is there and they’re going through grief. And I found it really emotionally and physically taxing to try to like do my job really well, but also recognise that it’s not about my job, it’s about these people that had suffered this. It’s kind of crazy that I continue to make these cases because while I’m doing it it’s very painful and uncomfortable. When I’m done I’m proud of it and it provokes conversation and I’m very lucky to work within an institution like HBO. But I don’t know why I keep doing it, I think I’m a little bit of a glutton for punishment. And now I’m known for this kind of stuff, so people send it to me. Before no one would respond to my emails, and now I might get a response, you know? So it’s just been a very weird unique five years.

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Was it always going to be a two parter? The first episode is so harrowing but the second is maybe a bit easier to deal with…

I found the second one so disturbing. The first episode is the case that you know and the second episode is the case that you thought you knew. And I think that a lot of filmmakers might do it differently and put a lot more of the crazy stuff in episode one, but I really trust HBO viewers that they’re going to be able to get to episode two. So it really was like, how do we flip the script and use the “I didn’t know that case. I didn’t understand it”. And so that was my objective.

What were the logistics, once you knew you wanted to cover the case, of talking to the Roy family and knowing you have all the elements in place to make this what you wanted it to be?

Yeah, it’s very sensitive. I very much knew that because it was very unlikely I was ever going to talk to Michelle Carter there needed to be a strong presence from the Roy family.

But when you look at my pieces – Thought Crimes, to Mommy Dead And Dearest they’re pretty sympathetic to the perpetrator. And so I think the Conrad Roy family was sceptical, rightfully so. And I remember when we hung out with his entire family and got to know him and really got to know him through his family I knew that there was a film there. I don’t want to ever speak for them but this has been so difficult. The documentary came out, millions more people are talking about it, and they’re talking about their kid, their Conrad.

It took many, many months to get them to do it, to say yes, then to actually film them took a really long time. It just was a relationship that was put together over a year and I think it’s always really difficult. I was able to show the film to Lynn before its coming out. I don’t know, I keep saying the word painful, I guess I didn’t know another way.

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I guess, when I do these interviews and people really like watching these films because it’s entertainment, but I think it’s sort of not entertainment. It’s heartbreaking. It looks like a polished finished project, but it took so many tears to get there.

The scenes with Conrad’s father where you talk about how Conrad had gone to the police after his dad had beaten him up must have been a really difficult thing to deal with?

Yeah, I was really physically uncomfortable at that moment, because it had been a part of the police reporting and had been part of the reporting that there was a physical incident prior to Conrad’s death. I think that he knew the question was coming. He had a really weird reaction to the question. Yeah, it was it was incredibly alienating for everybody involved in that room because I’m asking somebody did they hurt their son? But I think that I had to ask it. How can I not ask it? He answered in the way he thought was best.

Other than the Carter family, was there anybody that you wanted to talk to you that you weren’t able to, and was there was anyone that you spoke to that you had to cut out?

There’s a couple. I really would have liked to speak to her classmates, I think that would have been added context and clarity, but because of how vilified she was, nobody volunteered to do that. I talked to many people, I did it off the record, I just could not get people to go on the record, given how our society felt about her. I wish I had that, I wished I’d had the Carter family, but ultimately I think the film is unique in that it’s a portrait of two kids in real time, because we have the text messages. And I think we live in a world where access defines everything as related to documentaries. As you can see, like, you don’t need to have access to create a compelling piece of work.

I really am thankful to my mentors, Alex Gibney, Andrew Rossi and Sheila Nevins. You don’t need those things to make a documentary, even though it’s very useful and important to have it. But I think that you can’t always get people, especially with criminal cases, because people won’t specifically be allowed to talk to you.

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There’s a massive surge in popularity of documentaries, and how do you think documentary filmmaking has changed?

We’re living in this incredible age where people say, did you see Sid & Judy? Did you see Icarus? What did you watch last night? I’m like and it’s not just like a show like Glee, or The Good Place, people are actually talking about documentaries. And that’s crazy to me. I used to always go to parties, and people would say “what do you do?” And I’d say “I make documentaries”. And now when I say I make documentaries, people say “Ooh! Which ones!” From the most surface level, I feel really grateful that there are people like your readers who are wanting to think about these things and not like, not just Discovery ID shows but like really thoughtful, nuanced crime. Sometimes those shows are pretty thoughtful, but not always. So I just think the audience and the social media and the reaction to things are creating a pretty different climate to make films in.

Crime podcasts are massively popular now too. Some are great but some are made by people who aren’t journalists, or investigators, who are diving into cold cases and having theories, and having an influence when they aren’t necessarily qualified which makes me a bit nervous. Do you listen to podcasts and do you have any thoughts about that?

I think that’s a very thoughtful question. Are we detectives? Are we trained to investigate these things? Well the answer is no. I think that when you’re making a documentary and especially one like this, it has to be very closely verified and has to be vetted. And I think that for content to live out there, that is not being vetted in the same way is dangerous.

I think that if on a podcast you choose Uncle Joey – they think it was that guy who did it – be careful! Defamation laws are getting stronger. You know, we can’t call people out. I think overall podcasts are really good for storytelling, and I love listening to podcasts as an alternative form that I can just pop in while I’m in the subway. I listen to podcasts, I consume them. People have asked if I want to start one and I’m like I just can’t!

For this, documentaries, it’s so much time, energy and money, the cameras and all that. The thought of like speaking into a microphone about a story, there’s just a lot of promise and a lot of creativity in that.

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If you’ve been affected by the themes of this documentary or this interview here are some useful links:

Samaritans (for everyone): www.samaritans.org

CALM (for men): www.thecalmzone.net

Papyrus (for people under 35): papyrus-uk.org