SMIRK (audio version)
Chapter 12, Part 3: “Prey to a Prisoner”

Chapter 12, Part 3: “Prey to a Prisoner”

I get a fair amount of random personal questions from strangers about my life. Here is how I answered some.

Occasionally, strangers come across something about me, look me up online and send me messages asking detailed personal questions about my life. I don’t usually mind – I realize I brought this scourge upon myself.

As an example, I was recently going through and deleting a giant pile of unread emails dating back more than a year. I found one sent in May 2022 presumably by a person somewhere in the United States. The time stamp was 4:40am. The subject was just “You.”

“Ms. Smythe:” the email began. It then launched into a series of questions.

Was it enticing to be with a bad boy type? 

Was it a move to consciously or unconsciously flip-off the very industry you were covering (law, criminal justice, business, etc.)?”

Was it the thrill of leaving everything to begin anew?

Was it the excitement of falling prey to a prisoner - - an alleged con and manipulator?

Was it worth it? 

And so on.

The writer promised “no judgment here,” and I suspected none was intended. But the way some of the questions were worded suggested that someone’s judgment had infiltrated the person’s brain, through some medium or another. I studied the email thoughtfully, examining some of the more loaded language. 

A “bad boy” type? That archetype had existed in society for thousands of years, since the time when the earliest versions of “Little Red Riding Hood” and “Beauty and the Beast” were being told. Yes, I supposed, on some baseline evolutionary level, I was attracted to rebels, contrarians and “bad boys.” But so were lots of other people. 

A “move to consciously or unconsciously flip-off the very industry you were covering (law, criminal justice, business)?” I had to laugh at that one. I didn’t think I was “flipping off” anyone in those sectors by announcing I had been in a relationship with Martin Shkreli. I did offend some colleagues in the industry I worked in, the mainstream media, by doing so. But those who were most bothered – sanctimonious bullies who made their careers by mutilating facts and stepping on people  – deserved it.   

The “thrill of leaving everything to begin anew?” Honestly, my life had not really changed that much. I still worked as a journalist (try as some of the sanctimonious bullies might to proclaim that I had “torpedoed” my career, they could not stop me from being talented, capable and trusted). I still lived in New York. I still had most of the same friends. But perhaps I was more comfortable with change and uncertainty than most people, and that was why it became a fixation in my story. Also, maybe unlike many people, I preferred the unknown to unhappiness.

Then there was the phrase “falling prey to a prisoner,” which nagged me the most. It was steeped in assumptions. On the surface level, people often seemed to forget that I had not met Martin when he was “a prisoner,” but roughly two years before that. They tossed their preconceived, reality TV and true crime-inspired notions about “women dating prisoners” over me like an ill-fitting dress. And again, like in the old fairy tales, there was an image of a fragile maiden being stalked and manipulated by a villain, not of an adult woman making conscious decisions for herself.

The “falling prey” part was also annoying to me because it did not remotely match the facts. How on Earth was I “prey”? I left an ex-husband and a job because I had been unhappy with both. I chased after a dazzling and immersive romantic fantasy. I ended up with a divorce settlement, an apartment in Manhattan, a profile with a fashion shoot in ELLE, a 3D perspective of the media landscape and the legal system, and a lot of fascinating new acquaintances like Sydney Leathers

None of those things were what I had been aiming for when I started dating Martin, but they weren’t bad consolation prizes. In light of them, it would be extremely hard to call me a “victim.”

This email from Martin Shkreli to me while he was in prison shows he could be sensitive and romantic,.
This email from Martin Shkreli to me while he was in prison shows he could be sensitive and romantic,.

But I did not focus on any of those particular questions when I drafted my reply to the email writer. Instead, I looked at the shortest, simplest one: “Was it worth it?”

In truth, I had often thought about all the energy I had put into building a relationship with Martin – one that could exist in real life, away from social media and television cameras and headlines and a judgmental public, but which was solid enough to survive those things, too, when necessary. I had invested so much patience and dedication in him. I believed in him, I supported him, and I wanted him to succeed. And I, foolishly, deluded myself into thinking that all he needed was the right partner to do it.

I had never asked that he change, or “fix” his terrible public image, or live a conventional life, only that he make good on some of his promises and take a step toward me when the prison doors opened. The rest I could handle, ugly media spotlight, legal battles, endless parade of “side chicks” and internet admirers and all. But then he didn’t. I wondered if it was all a waste. 

Then I remembered what had nudged me toward him in the first place: an almost instantaneous and pure interpersonal bond. It was the kind where you can go years without speaking but still be able to finish each other’s sentences. It was the kind which clearly transcended what he and I were supposed to be to each other in other people’s eyes. It was the kind of connection which adds joy and meaning to life. It was worth pursuing and exploring.

 The things I left behind were hollow and pedestrian by comparison. A marriage that seemed to be more about acquiring material possessions, going on expensive vacations, and acting the part of a perfect couple for Instagram rather than on building a harmonious partnership was not a loss. A job where I felt like a cog in a machine, a hamster on a wheel, and a pawn on a chessboard, where my talents were stifled by thick layers of office politics and paternalistic sexism, was not a loss.

If I were to be confronted again with a stark choice between love and a big media career with financial security, I would pick love again without hesitation, even if it was far from a sure bet. Some things are just more important.

A Whatsapp message between myself (in green) and Martin Shkreli (in white) while he was in prison. He used the pseudonym “Dan Iriving.”

In my reply, I wrote:

Honestly, it didn't matter all that much to me that Martin was a "bad boy" type. We had a connection (maybe past tense, but it was there) in which we saw and respected each other as individuals. If you've ever met someone who just "gets" you, who you could literally talk and laugh with for days on end and never run out of things to say, while also being perfectly at ease and never feeling like you "have" to talk if you don't want to....well, if you've ever had that, then you know it doesn't matter how society views this person, or you, or any of the other externalities. 

I did not have that with my ex-husband. I thought I would when I married him, but it just didn't work out. I also didn't feel as respected in my own industry. Now, there are people in my industry who definitely don't like me, but many of them also realize I'm a force to be reckoned with. So yeah, it was worth it.

Check out other recent SMIRK posts: 

Chapter 12, Part 2: "High-Splash" Schizoid

Chapter 12, Part 1: Cruel Intentions

Chapter 11, Part 3: Justice is Zugzwang

Chapter 11, Part 1: Burning a Source

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SMIRK (audio version)
My experiences uncovering the story of, and falling in love with, Martin Shkreli.