One of My Dating-App Matches Just Wanted to Talk, So We Became Pen Pals

I forgot how nice it is to talk to a stranger when there aren’t any expectations.
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Dana Hamilton
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I forgot how nice it is to talk to a stranger when there aren’t any expectations.

There are a few things I find to be as addictive as the dating app Bumble: peeling off sunburned skin, black tar heroin, Pringles (any flavor), and gambling. So let’s just say that, over the past year, I’ve dated a lot and leave it at that. 

Like anyone else who’s been dating for a while, I’ve learned a lot about myself — most notably that I am attracted to recently divorced Scorpio men. I don’t know how they all find me (maybe there’s a secret society where they all get together and lie about their feelings), but I am like catnip for Scorpio divorcees.

After a particularly sad breakup with a divorced Scorpio I’d been sleeping with (I wouldn’t exactly call it dating), I did what any normal woman would do: went to Babeland with three of my best friends and dropped some major coin, then headed back to my friend’s apartment where I got drunk, ate way too much Thai food, and charged my new vibrator on her kitchen counter while I live-tweeted my first time watching 50 Shades of Grey from my corporate Twitter account. You know, what most people do. 

I also re-downloaded Bumble on my phone.

The next day, hung over and burping up spring rolls — after I’d frantically deleted all the things I tweeted the previous night, including “just ONCE would I like someone to ask me to strike out ‘anal fisting’ on a contract” — my pointer finger started its usual ballroom dance across the screen of my iPhone. 

After a few minutes of swiping, I started talking to a guy who had a really cool job that piqued my interest. A foodie, I asked about the cooking skills he mentioned in his profile. He told me about the goose he smoked for Thanksgiving (to which I replied, “Who are you, Bob Cratchit?”) and because I’m a star child or, you know, just a big dumb idiot, I asked him his sign. And surprise, surprise: SCORPIO. 

He asked what I do for a living, which, as a writer who predominantly talks about sex and body image, the easiest answer I could give him was: “I talk about my butthole a lot.” I even wrote a limerick about his butthole to prove that I’m worth my salt. 

It was all going so well.

It was all going so well.

But then we kept talking, and it came up: Ryan was divorced. And not just recently, but VERY recently. In fact, the divorce was finalized not even a month ago. I rolled my eyes. Again? I thought. This can’t be happening. 

And so I told him, to paraphrase, Hey, it was nice talking to you, but I can’t mess with someone so recently divorced. Be well, take care of yourself, best of luck. 

And that’s when he said something that made me stop in my tracks:

Ryan asking me to keep him around.jpg

My knee-jerk reaction was, “Whoa, how manipulative is this guy?” Well, that’s a lie. My real knee-jerk reaction was gut-busting laughter. Asking if I can “keep him around” even though I’ve already told him no? I’ve played this game before. I tell someone I don’t want to hang out and then they say, “No problem, we can just keep talking,” and then we do and they eventually wear me down. Next thing I know, I’m at their apartment bent over with my pants around my ankles swearing I’m never going to fall for this again. 

Call me jaded, but I just didn’t trust that Ryan was being honest with me.

But then I took a step back. I’ve never been divorced before, so I have no idea what it’s like to go through that. But have I ever felt lonely? Sure. Have I ever been so hopelessly bored by 99% of the men I talk to that I get excited about the very, very few I have a fun time chatting with? Absolutely. Have I ever felt overwhelmed while navigating my way through the dating world? Yes. Have I ever had a painful breakup? Of course.

And so I thought, okay, maybe I won’t shut this guy down. This is just a dude who wants someone fun to talk to, and it’s not like I didn’t enjoy talking to him. What did I have to lose, really? 

And so I made a suggestion: what if we were pen pals? If he really did want to just talk, this seemed like a viable alternative. And if he really was trying to manipulate me into going on a date, I could just stop the correspondence whenever I wanted.

pen pal suggestion.jpg

At first, Ryan didn’t know what to do with the idea. Obviously, he wasn’t expecting such a proposition. After talking it over and going through the specifics, to my surprise, he agreed.

I had a five rules:

  • We use each other’s work addresses instead of home addresses (both of our offices have a crazy level of security, so we felt safe providing these to each other).

  • We do not talk about the people we sleep with. I didn’t want to take it to that level.

  • Each letter has to contain a few questions for the other to prompt what we talk about in the next letter. I told him, “Be unique. If you ask me my favorite color or something, I will legit tear your letter into strips and use them as rolling papers.” The last thing I wanted was another round of “Hey, what do you do?” “Where are you from?” aka the questions I answer over and over and over again on dating apps. I wanted this to be fun and original. He agreed.

  • We end each letter with a drawing or photograph.
  • We write each other once a week. I put this rule into place so that we each had an understanding of the frequency and because I wanted to make sure he didn’t Harry Potter my ass like that one scene with the Hogwarts acceptance letters flooding the chimney.

So far, that’s exactly what we’ve been doing. About once a week, Ryan and I exchange letters. And you know what? It’s been fun. The topics we’ve talked about have run the gamut: everything from family secrets to the idea of marriage (his disdain for it, my love for monogamy so I don’t have to get tested as often) to what we’re working on in therapy. We talk about how weird our friends are, who inspires us, the personality traits we like the least about ourselves, our favorite comedians, what we do for self-care. We psychoanalyze each other. We give each other advice. We make each other laugh. I’ve told him things I’ve never told anyone else, and he’s admitted the same is true for him. We don’t flirt with each other. We have no plans on meeting up in the near future. We write each other because we want to.

I forgot how nice it is to talk to a stranger when there aren’t any expectations. Getting to know someone without the stress of waiting for them to return your text messages, agonizing over the pimple you picked 10 minutes before a date, analyzing what they said over and over in your head, trying to decode what they really mean. Dating is stressful. But when I read Ryan’s letters, I take them at face value and respond without any self-consciousness or second-guessing myself. I’m pretty much the most authentic version of myself when I’m writing. I don’t edit anything, I don’t censor myself in any way. I don’t overthink anything.

The first time I wrote Ryan, I found a card in my stationary collection that was perfect. Also, I’m just kind of an asshole. Thankfully, he has a great sense of humor and found it funny.

The front of the card.

The front of the card.

At the end of my first letter to him (which I folded up and stuffed into that card), I included a picture of Rick Astley and told Ryan I chose the image because “I'm never GONNA GIVE YOU UP, Ryan. NEVER GONNA MAKE YOU CRY. NEVER GONNA TELL A LIE AND DESERT YOU.” We’ve been pen pals for a few months now and we may never meet up, but one time we made an unbinding agreement to meet up for dinner after a year. (A one-year pen pal-iversary, if you will.) Is it more than likely that one of us will find a partner before then and have to call this whole thing off? Probably. But, for now, it’s been really interesting getting to know another human being.

Inside.

Inside.

I could have very easily unmatched Ryan, and the likelihood of me ever running into him in real life would be the same chances as me winning a Powerball jackpot. I think about that a lot. Being on dating apps is mentally taxing. Sometimes it’s really hard to keep your chin up. But if you think of weird shit to do to prevent yourself from going insane, it can be a lot of fun, too. You may even make a friend.