My College Love Sent Me a Mysterious Message, 25 Years Later

I think he’s going to a North Korean prison.

If you can’t understand anything I write, it’s because you have to read over the sound of me shoveling a huge pack of Costco chocolate chunk cookies down my throat from stress and confusion. This situation needs carbs.

Last year, I received an email from my high school boyfriend apologizing for being a piece of shit to me. This is about damn time, given how he made me think I was exposed to HIV and strung me along when he was with someone else.

Today, I received a random cryptic email. Typically, I’d copy/paste here but I noticed that he’s written at least once on Medium and I don’t want to risk him finding my writing.

The email barely made any sense. It sounded like the rantings of a drug addict handed a phone for a few minutes. I guessed as to who sent it because my college boyfriend is extremely successful (millions upon millions kind of thing) and it would make no sense for a brilliant intellect to send something as incoherent as a donkey reading Shakespeare.

Ross and I dated for most of college. He was born with a silver spoon and in everything he did, he had incredible luck. Casinos, stocks, you name it. He could make money by snapping his fingers. Ever the charmer, he schmoozed women everywhere which fed my insecurities. Ross was in the top 5% of our graduating class. I was at the bottom 5% (in my defense, I didn’t pursue the subject I was actually good at) and piggybacked off his projects to pass.

When we graduated, he immediately applied for grad school. I applied for a job out of the country. Needing to run away from my overbearing parents at 23, I left and gave Ross the choice: come with me or do your Masters. I heavily pushed the Masters option because no one should give up education for a love interest.

We formally broke up after I lived in California for a few weeks. I cried that night. I cried the next morning. Then I did my road test to get a US driver’s license. I passed. My care factor over the breakup dropped to zero over the good news of my road test.

According to LinkedIn and dozens of published articles, Ross moved on and became extremely successful in his career. He got his Ph.D. and filed some patents. As for me…well, I’m here on Medium baring my soul.

Here is my paraphrased attempt at his email for the sake of anonymity.

Remember (insert name of song)? Remember this? Remember that?

I created this fake account to get in touch with you, J.

I want to make sure you’re okay but I have no way to safely get a response. Please don’t contact me outside of this message.

I’m leaving for a far away land. I achieved all my goals and dreams but I’m leaving for annoying nondescript reasons.

When I was turning into an adult, I didn’t expect you. You deserved better than what you got (apologies). Success was always more important than relationships. You were like a bolt of lightning and I wish you hadn’t left for California. I wish I had gone with you. What was I thinking? This is the “everywhere, all at once” plot I want to see. Don’t leave.

I came to California many times. I thought I’d shoot my shot when I wasn’t under lock and key. But it didn’t happen. I visited x, y, z cities and thought I could stumble into your work. See you, get a hug, and a kiss on the cheek.

I’m leaving now for a long time. I might not be reachable even when I come back. I’ll be old by then. I think of you and I wish you well. I wonder if you think of me too.

This is a random message, I’ll check back now and then to see if you replied.

What the actual fuck message is that? If it sounds confusing believe me, the non-paraphrased version is no different.

Being the impatient asshole that I am, I didn’t ponder for long. I immediately wrote back and said, “What is this effing cryptic message? Just call or text me.” I include my phone number.

Within minutes, I get the call.

“Hey,” he begins. “It’s Ross.” Yeah, no kidding.

I begin my tirade. “So, what the hell? Are you leaving the country because you’re going to get murdered or go to prison?”

Ross babbles about something nonsensical. I completely forgot that he’s a pie-in-the-sky guy who creates visions without implementing anything. Truly, the mark of a great leader. No wonder why he’s a bigwig at every company.

“Seriously, shut up,” I interrupt. “Are you leaving because there’s criminal stuff going on or because the government is after you?” When we met, he was a rich high school kid who swindled money with an internet pyramid scheme which he got out of courtesy of his fancy lawyer dad. He also made money by illegally photocopying college textbooks and selling fake drugs to unsuspecting teens.

“You know me. Always criminal,” he replies. Ross goes on another nonsensical rant.

I ask him if he’s drunk or high. He insists that he’s neither but the entire conversation is stilted and convoluted.

The gist of the conversation is that Ross made millions. He would give it all up to go back in time and fight to keep me. I told him that I was just a selfish kid who didn’t grow up until she had children. He tells me he doesn’t care, that we could have grown up together, and that he should have supported me more.

I tell him, “Honestly, I don’t bear any ill will against you. The only bad-mouthing I have is that you’re the only guy I let cum on my face and you got annoyed that I squinted because it ruined it for you. Cum is impossible to get out of hair, do you know how hard it would have been to get out of my contact lenses?”

Ross tells me how I shaped his sexual identity. I apologize for not trimming the hair between my legs better back then (it’s all lasered off now). He tells me how nice and great I was back then. I tell him that it wouldn’t have worked because he would have cheated on me with one of the many blonds he was obsessed with. For every compliment, I give a snarky reply.

We chat about a few small events, things that both of us forgot. He reminds me of meeting my brother and one of my favorite restaurants. I remind him of the varsity jacket his dad’s receptionist gave him and how his father paid for his sister’s tattoo removal. I also remind him that he tried to use his ex-girlfriend’s dildo on me. “I promise you, I’d get a new dildo if I ever had a night with you,” he replies.

In college, I did almost anything to please Ross. I’m the classic psychological trope of the girl who lacked her father’s presence and seeks male attention to determine her self-worth. As for Ross, anyone with him was in his shadow because he was the shining star. I couldn’t compete.

The conversation leads to things I still have from him. A necklace, some rings, and one piece of lingerie. To add salt to injury, I told him I wore the lingerie in a naked photoshoot a while back. “You wouldn’t have those pictures laying around, would you?” he asks. There is no planet that I’m sending those to him.

I find out that he’s not going to prison in a fascist country or escaping a mob boss. Ross has a new job in Milan. “How the hell does that mean you’ll be a changed person? From eating all that pasta and wine?” I snap.

The reason he’s acting like he’s on the run and must be discreet is he doesn’t want his wife to find out. I suppose an enraged wife is as terrifying as Pablo Escobar. He married her because being career-driven to the top means any woman with him has to forego her dreams. Ross married an “executive wife”, which is a woman who gives up her career aspirations to be his supporter. They don’t have any kids.

“You know that you moving to Italy is no different to me than you staying in Canada, right? It’s not like I’m visiting you. Your location is irrelevant,” I remind him. “I’m too poor to try and stalk you in Europe.”

I still don’t know what he’s expecting out of this conversation. Since I work from home and it’s a non-custody day, I had plenty of time to venture down this bizarre rabbit hole. It’s amusing and confusing all at once.

“I just wanted you to know that when you write me, it might take a while to answer back,” Ross delicately whispers. Unlike him, I have no problems talking at full blast like a bull in a china shop.

“Why would I even write you?” I yell. “I mean, I’ll reply if you send me something, but I’m not going out of my way to send you random messages. Also, I have dozens of Gmail addresses, it’s not hard to send a message to someone without a spouse seeing it if you have more than one email.”

Ross tells me that he knows I’ll message him first because curiosity will get the best of me. “Nope. You underestimate how little I care to write you out of the blue,” I reply.

A text from an appliance repair man saves me from the call. We say goodbye and hang up. Sitting on my bed, I’m stunned.

Why are these boyfriends coming out of the woodwork now? Why are they suddenly filled with regret for our breakup (as if young romance would have lasted into adulthood)? Do I have residual mojo?

These early relationships formed much of my personality and my behavior in relationships. My self-esteem in my youth was tied to how I wasn’t everything that someone else wanted. I wasn’t the cool goth girl. I wasn’t the chill girl who did pot. I wasn’t a white chick with blond hair. I didn’t have parents who let me date and would invite boyfriends over for dinner. I wasn’t allowed to wear revealing clothes and occasionally snuck out with a long skirt to cover my short dress.

Ross had said, “Sometimes we went out for dinner and you’d wear short skirts for me. I know how uncomfortable it made you but you still did that for me. I really appreciate that.”

I don’t remember that at all. I was adorable back then and yet, I loathed my body like a vampire to garlic. I cried at my perceived imperfections. Now, all these years later, I only wear short skirts on dates and sometimes feel confident about my appearance.

I’m not the same person Ross remembers. I’m so grateful that I’m not.

As I go to hit “Publish” on this article, I get an email from Ross. In the game of email chicken, he lost within an hour.