HBO’s I Love You, Now Die is a Complicated, Must-Watch Documentary

When I was 16, I acquired two important firsts: my first girlfriend and my first cell phone. The two entities were basically inseparable in my mind. Even though my girlfriend lived in the same town as I did and attended the same school, I would wager that 80% of our conversations existed via text messaging on my silver Motorola. 

We were always in contact, texting messages that contained deeply philosophical (or so I thought) musings on our shared love and also the most inane bullshit imaginable. My mom once had to have an intervention with me as our shared cell phone plan was reaching an astronomical cost. I toned down the incessant texting as best I could, but in the end, my mom just had to cave and spring for an unlimited text plan (which were rare in those prehistoric days). 

As time went on, whether I realized it or not, my girlfriend had become my living, breathing diary. My entire life was contained within those texts, to the point where I decided to archive them, writing them down by hand in a little notebook. It didn’t occur to me that there was any other way to save them. My figurative diary had become a literal one.

further reading: The Best Documentaries on HBO

The combination of my hormones, another human being, and this brand new technology created something obsessive and dangerous. We decided to break up before college and when I discovered that my diary was suddenly gone and my phone’s inbox, empty, I begged for her back. We went to the same college together, lasted for two quarters and then broke up again: for real this time. I had made no other friends. I was left with nothing but an empty phone and the strong desire to be dead. 

Eventually, I climbed out of that teenage depression, made some friends, grew up, and developed more healthy relationships with both women and technology. But that memory of techno-hormonal obsession has never left me. And it’s something that I remembered again while watching HBO’s excellent two-part documentary, I Love You, Now Die.

I Love You, Now Die, from ace documentarian Erin Lee Carr (Mommy Dead and Dearest), tells the complete story of an event that most people have at least a passing familiarity with. In July of 2014, 18-year-old Conrad Roy’s dead body was discovered in his truck in a Kmart parking lot near his home in Eastern Massachusetts. Roy had killed himself via carbon monoxide poisoning by piping the fumes from the back of his truck into the cabin. 

When investigators on the scene unlocked his phone, they found something astonishing. There were thousands upon thousands of texts from Roy’s (sort-of) girlfriend, 17-year-old girlfriend, Michelle Carter. Michelle had texted Conrad dozens of times the day of his suicide, encouraging him to go through with his self-destructive plan. A sampling of these texts read “You’re ready and prepared. All you have to do is turn the generator on and you bee (sic) free and happy. No more pushing it off, no more waiting” and “You’re fine, it’s gonna be okay. You just gotta do it, babe, you can’t think about it.” 

Investigators later confiscated Michelle’s phone and found other messages sent to some of her peers and classmates indicating that Conrad was dead because of her and when his nerve waned, she said she even encouraged him via phone call to suck it up and get back in the truck. 

Understandably, the case struck a nerve, popping up on many true crime programs dissecting how a child could do something so malevolent and manipulative to another child. The case of Michelle Carter and Conrad Roy is often seen as a tattered symbol of “The Way We Live Now,” “The End of the Youth of America,” and the Black Mirror-esque “It’s Because You Be on That Damn Phone.”

It’s a shocking, confusing case and an even more shocking and confusing story. It’s precisely the kind of thing that is crying out for a capable documentary to examine with little bias and tremendous empathy. Thankfully, that documentary is now here with I Love You, Now Die.

There’s no such thing as a purely objective documentary because there’s no such thing as a purely objective person. All documentarians bring with them their biases to the door. The best that any viewer can hope is that those documentarians do their best to rein those biases in. In I Love You, Now Die, Carr has done a wondrous job of doing so. This feels like a fair, sober examination of what happens when two damaged youths make a connection via a technology that doesn’t require them to see each other face-to-face. 

further reading: The Best True Crime Series Available to Stream Right Now

As one expert notes in the show’s second half, “With two people communicating through text, strange things can happen. You don’t necessarily experience the other person as another person. You can’t see them, you can’t hear them. You can’t see their body language. You have them as this voice with you all day long. I think some people experience it as a voice in their head, almost like a hallucination.”

I Love You, Now Die borrows the two-part HBO documentary model from this winter’s excellent Leaving Neverland. The first part of the documentary mostly examines the case from the prosecution’s side and airs on Tuesday, July 9 at 8 p.m.. the second part focuses on the defense and airs the following night, Wednesday, July 10 at 8 p.m. Various talking heads in the first hour make no excuses for Michelle’s behavior on the fateful day in question. Some, however, plead with the viewer to view Michelle and Conrad’s relationship in its entirety, rather than just its final chapter. The documentary’s second half, in particular, does a marvelous job in painting the picture of the whole relationship. That picture is believable, tragic, terrifying, and blurs the concepts of the victim and the victimizer as we understand them. This is a thoroughly modern, technologically-enabled case of foile à deux.

I Love You, Now Die feels like a two and a half hour cry for help from a younger generation to an older one. Back in my high school days when I was engaged in a turbulent relationship with a woman and a phone, I was still relatively “old.” I’m of the last generation who actually remembers what it was like to live in a world without mass adoption of communication technology. When that phone and the woman on the other side of it fell into my ways, I had enough phone-less life experiences built up to in theory understand what a world without constant contact felt like.

I can’t even begin to imagine what it was like for future generations. I’m not saying that cell phones are evil. But they have changed the experience of growing up for young people in ways that older generations can’t even begin to comprehend. The experience of watching I Love You, Now Die is the experience of watching older folks realize, in real time, just how big a role both constant connection, and weirdly, suicide ideation plays in the development of young people. 

Michelle and Conrad met in real life only a handful of times and almost the entirety of their relationship existed as little text bubbles in the palm of their hands. As depicted by the documentary, Michelle and Conrad’s relationship was more mutually exploitative rather than just one party harassing the other into suicide. Michelle, a desperately lonely and mentally ill girl, relished the idea of having someone in her pocket who she could call her boyfriend (even if that wasn’t a title Conrad always granted happily). Conrad was excited to have a human diary on the other end of his phone, to soak up the details of his many suicidal thoughts and attempts. The Romeo and Juliet comparisons come quick and easy. This is a story of if Romeo and Juliet were each in love with death rather than each other. 

In looking for the definitive stories of particular eras, sometimes it feels like true crime is the only place to look. I felt that watching both FX’s brilliant The People v. O.J. Simpson and ESPN’s equally brilliant O.J.: Made in America. The O.J. Simpson case feels more like the crux on which all of American culture turns more than any fictional entity ever could. The O.J. case represents the most extreme time that America had to confront its own relationships with race, misogyny, and celebrity. It’s not unreasonable to draw a straight line from America not learning the lesson that sometimes it’s ok to not be entertained at every single moment of the day to the world we live in today. 

I Love You, Now Die tells the real-life story that has potentially the most similar generational impact to the O.J. Simpson case. Where the O.J. case was a perfect storm of celebrity, 24/7 media, and racial tensions, the Michelle Carter is the perfect storm of cell phone technology, suicide, and fear of eerie teenage girls who would do anything to make a friend. We never learned our lesson from the O.J. trial, and I’m not entirely sure what lessons there are to be taken away from the Michelle Carter/Conrad Roy case. But I do know that all the material we need to learn whatever lesson there is to learn from this case lives in I Love You, Now Die.

Alec Bojalad is TV Editor at Den of Geek and TCA member. Read more of his stuff here. Follow him at his creatively-named Twitter handle @alecbojalad