Stephen Newman

Is Your Pen Pal Too Clingy? by Stephen Newman

“I just received your first letter and I already can tell I’m falling in love with you.”

“I know you just started writing me last week, but you are the most amazing person I’ve ever met. We have so much in common.”

“Thanks for your email. Would you ever consider leaving your husband and marrying me? Also, how old are you?”

If any of the above sounds familiar, my guess is that you’ve written to a penpal who became too clingy, too fast. Several people have asked me to write a blog entry on this subject — the clingy inmate penpal.

In lieu of my manufactured quotes above, they might have sent you love poems, a rose made out of toilet paper, handmade jewelry, a jewelry box made of potato chip bags, a hand-drawn card with plenty of hearts and ‘I love you’s’, or maybe even a 60-page manifesto telling you exactly how and why YOU are the most amazing woman in the world. And I can imagine your reaction was, “Oh my God, what have I gotten myself into with this guy.”

After your pencil-sketched portrait arrived, you may have even told yourself, “My (sister, mom, friend) was right, I should have never written to an inmate.”

Before we criticize too much, I must confess that I, too, have been guilty of overexuberance toward a brand new penpal. While I haven’t proposed marriage on my second letter, or anything over-the-top crazy like that, I have had a woman politely inform me that I was artificially speeding up the “getting to know you” phase.

She wrote:
“You mentioned how I’m one of the few people you trust…part of me is flattered, and the other part of me wonders how that could be? I mean, we’re just getting to know one another.”

The question becomes why? Why did your penpal fall in love with you in a week? Why did you think you were just casual acquaintances, then were shocked when he sent you a love poem and some jewelry? Why did I tell someone I had just met that she was “one of the few people I trusted”?

Throughout your day, in the free-world, you probably deal with dozens of people of the opposite sex. You go to work and talk to your boss and co-workers. You have a quick conversation with the sandwich artist at your neighborhood Subway. You watch movies with your spouse. You have a parent-teacher conference at your kids’ school. You buy concert tickets from some stranger online, and meet them at some gas station adjacent to the freeway to facilitate your shady transaction (“Um, hey, are you Jeff? Hi, I’m Amanda. We said $220, right? And you’re sure they’re the 11th row?”). You probably also text a variety of people each and every day. Your inmate penpal is just one of 50, perhaps 100 connections you’ve made that day or week. So in your mind, he takes up no more than 2 percent of your thoughts…probably much less.

Now, let’s flip the script. The inmate — he sits in his bed watching TV, waiting for chow. He showers. He reads his Prison Legal News magazine. He plays videogames on his tablet. He reorganizes his locker. He doesn’t see, write, or talk to any woman…often for months at a time. And then, it happens — a woman expresses interest in him. I mean, he gets the envelope or reads the name on JPay, and it doesn’t matter if it says Amy or Becca or Christina or Diane or Elena. It’s a woman’s name, a woman’s writing, a purple pen, maybe the letter even smells like perfume. He hasn’t even opened it yet, he knows absolutely nothing about you, but already this is the best thing that has happened to him all week.

So while you go about your daily routine, with 100 people in your real-life social network (and probably an ungodly amount of Facebook “friends”) you may think of this inmate every now and then. Conversely, after he reads your letter, you are ALL he thinks about that night, the next morning, the next day, and the next. It doesn’t matter if you’re 18 or 58, it doesn’t matter if you’re fat or thin, it doesn’t matter if you’re married or single. You’re a female, and he is like a dry sponge just waiting to soak up your friendship and attention. Wanting to learn more about you. Wanting you to like him.

He becomes afraid of losing you, afraid of being abandoned. Because let’s face it — he has likely been abandoned before. Probably by a lot of people. When he got arrested or sent to prison, he may have been abandoned by his family, his friends, his business partners, his girlfriend, perhaps even his children. And the odds are good that he’s been abandoned by at least a few penpals before you.

He likes you. As he reads your letter, you are his life — his entire life — and he is so afraid of losing you that he ends up overcompensating with letters, drawings, gifts, comic strip clippings from the local newspaper, anything at all to help him feel special and needed and appreciated. His attention scares the shit out of you. That’s understandable.

But before you blame the inmate entirely, you might consider carefully examining your own motives and reasons for writing him. Most (not all) women who proactively decide to write to an inmate via a penpal website do so because of their own low self-esteem and lack of confidence. They write because they know they’ll have less of a chance to get rejected by an inmate (because, let’s be honest, he is starved for affection and they know that). Otherwise, they’d be on Match or eHarmony, not WriteAPrisoner.

Some women also write inmates because, ironically, it’s safer. Often they are unhappily married and crave an emotional connection without the risk of it turning into a physical affair. The inmate tries to give them what they need, but he moves too fast, he comes on too strong. He clearly needs a refresher course on playing hard to get.

Most inmates mean well, we really do. We try our best, and often fall short. My advice? Just be honest. Tell him to slow down. He will listen.

–Sign up to email me at–

Stephen Newman
DOC #90843


Categories: Stephen Newman

3 replies »

  1. It’s somewhat presumptuous to assume that women (or men) on the outside have countless interactions both small scale or otherwise in their every day life. Many do, but many don’t. Some are busy single parents who go to work and then come home and work a second job as parents. They often have no one to care one bit about them or their feelings or thoughts. and sites like it are places NOT looking for pen pals. Many ads on there state they are “not looking for a pen pal”. Some are so uncouth as to say they are looking for someone for “fun times only” and send a photo of their genitalia within the first 24 hours. One need not be alone to feel lonely. I think loneliness has got more to do with no one taking a genuine authentic interest in you. Everyone yearns to feel connectedness with people. Prison is an environment which brings this issue to bear more quickly. Great post , thank you


  2. I can absolutely see where the different perspectives come from. It can happen on the outside too, where one party is occupies a bigger part of the other’s life, bu prison must just make blow it up to ridiculous levels.

    Liked by 1 person

  3. LOL Fortunately any penpals I have are close to my husband and respectful of his wife but this post really made me LOL. I have a clingy penpal but I share his name so I guess it’s alright! 😂


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