Letter writing tips. Are you getting bored and boring your pen pals too?

As an active pen pal for 35 years, I’ve heard a certain letter-writing “complaint” a few times. Individuals who are getting tired of the pen pal hobby because it has become boring, writing the same thing over and over again to everyone. “I did this and I did that.” — What’s the point? Well, yes, writing the same thing over and over again to every pen pal would indeed become rather boring and pointless! There is no point.

Writing letters should be about forming a friendship, not just about getting mail. I think  some pen pals have forgotten about the friendship part. It seems that generally in our society, not just with the pen pal hobby, friendship has become a lost art. I’ve had related posts before, but this time I wanted to share some letter writing ideas so that you don’t end up writing the same thing over and over again.

⇒ While I do share my life news with my pen pals, I rarely write the same thing in the same way to each and every one! Know your pen pals. Each pen pal is a unique individual. There are things you share in common with them, and things that you do not. There are ways you are the same, and ways you are different. Keep this in mind as you write a letter!

I may write a long and detailed description about something to one pen pal, but reduce it to a 2-sentence summary to another pen pal. I know that one will find it interesting, and the other will find it boring. There are “areas” of my life that I share frequently with certain pen pals, but with other pen pals I only bring these areas up on occasion.

⇒ If your letters have become mostly about life news, bring something else up! Ask a question, and share your answer too. This is limitless, really! A few ideas…How would your pen pal describe their personality type? If they were given enough money to travel anywhere, where would they go? If married, how did they meet their spouse? When is a time they remember laughing their head off? What are some things in life for which they are thankful or grateful? Ask them about some of their “favorites” such as favorite movie, book, food, color, etc. Do they have any pet-peeves?

⇒ Finally, as I have often emphasized, a letter should be more than sharing your news. Respond to their letter. A letter should be a dialogue, not a monologue. Maybe you have a question about something they wrote about. Maybe you related to a problem they shared, and you can commiserate a bit. Maybe you really enjoyed hearing about their vacation, and you can simply let them know it. Etc.

I hope that gives you some ideas for keeping your letters varied and interesting, developing a friendship, and not being like a…robot…mechanically writing the same thing over and over to every pen pal!

What if you did not have pen and paper but had to use an iron stylus to press into a clay tablet?

A correspondent sent me this clipping (below) from an archeology magazine. Imagine if you had to use an iron stylus to press letters into a clay tablet! You can click on the article to enlarge it and read it.

We have it so easy – a huge selection of pens and plentiful paper! So, what is your excuse for not writing a letter? Write a letter today! Here is a review of my favorite pen that I wrote a while back. It remains my favorite pen!

Also, if you end up staying home more to avoid the flu or coronavirus, why not utilize the time by writing some letters? Perhaps write notes to people besides your pen pals. In recent years, I mostly write letters to my pen friends, and I need to write notes to others more often. Here is a sensible article from Scientific American about preparing for the coronavirus.

Think of a letter as a visit with a friend over coffee!

I once had a post entitled: Are you writing a friend, or only writing a letter? There is a difference! Are you just dashing off letters because you like to get mail -or- are you trying to develop a friendship? I’ve always considered my pen pals to be friends that I want to get to know.

Related to this, I also had a post emphasizing that letters should be a dialogue, not a monologue. Someone shared: “I want conversational letters. Not looking for people who only write about themselves and ignore everything I write.” In other words, friendship should be a two-way street, where two people are mutually interested in one another.

In the last several years I’ve encountered a new (but related) “problem” with pen pals. Pen pals who may write dialogue letters, but seem to remember nothing from previous letters! It is almost like each letter you write them is the first letter they have received from you!  It has been a pattern with certain pen pals.

I’ll offer one example, so you know what I mean. I wrote a pen pal telling her all about a vacation I took to another country. She replied. In my letter back to her I enclosed a postcard from the country I visited, as I forgot to send it before. She replied, something like “Wow! I did not know you visited this place. Please tell me about your vacation!” – Uh, I already did in my previous letter!!

We can all have slips of the memory. None of us can remember everything a pen pal has shared with us in previous letters. But that is NOT what I am talking about, rather I am talking about a pattern – it happens repeatedly.

Has the hustle and bustle of modern life invaded the pen pal hobby? Postal mail is supposed to “slow you down” – Picking up a pen and writing a letter is different than sending a text message or making a phone call. At least it should be!

There are also studies/research that indicate that the internet is affecting our reading abilities. Our brains become so accustomed to skim reading short articles on the internet, that we are losing our ability to read deeply. Our minds jump from thing to thing, rather being able to focus on one thing. Maybe this is part of the problem too? Some pen pals are not slowing down, only skim read their letters, and dash off replies.

Before I lose you (this article gets long for internet reading!) here are some ideas for being a better pen friend. How can you remember more of what your pen pals have shared with you in the past? How can you be a better friend?

♥ Read each letter more than once. I read a letter when I first receive it. However, I can rarely reply immediately. When I later go to answer the letter, I read it again. And…

♥ Take time to think about the letter. What do you relate to? What do you have a question about? I am a practicing Christian, and if my pen pal is having a struggle or problem, I may take a moment to pray for them. Commiserate. The point here is to slow down!

You are more likely to remember things when you take time, rather than being in a rush.

Think of a letter as a visit with a friend over coffee! 

♥ Some pen pals utilize pen pal “info cards” to be more organized with their pen friends. I use 3 x 5 cards, but others use sheets of paper. In case you are not familiar with this, you ask your pen pals to fill out an “info card/sheet” for you. On it, you have basic categories of info such as: name, address, birthday, children, pets, hobbies, collections, favorite color, etc. This gives you a “snapshot” of your pen pal – essential things about them to remember.

This can help you in the future! If you forget (“Uh…does Julie have 3 cats or is that Mary?”) – you can review your info card.  I also “update” my cards myself when a pen pal tells me something new that I want to be sure to remember. Maybe a dear pet died, a new grandchild is born, or they have gotten involved in a new hobby.

None of us has a perfect memory, and my “info cards” help me be a better pen friend.

This post grows long, so I will bring it to a close. Slow down, and consider how you can be a better friend.

More first letter tips to that potential new pen friend

I already had a post with tips on writing the first letter to a potential new pen friend. See here. However, I did not emphasize the potential aspect in that post, and I will also offer another first letter tip as well.

#1 Someone may not write you back for a variety of reasons, and you should have a reasonable expectation. Don’t take it personally if they don’t write back, as it could have nothing to do with your letter. They could have had a change in their life circumstances or already reached their pen pal quota. And don’t be demanding, assuming they will write back – it is their option to do so. Maybe they just did not “connect” with your letter, not feeling you had enough in common to correspond.

I recently received a first letter from an individual wanting to be my pen pal, and I was taken aback by several things. But one was this…Several times in the letter the person made rather demanding comments along the lines of expecting to hear back from me and that they had faith I would reply. It actually made me a bit uncomfortable. For several reasons I will not reply, and I wonder if they will mail me more letters demanding to know why I have not replied? Hopefully not! We shall see.

When I write a first letter, depending on the situation, I always say something about the potential of hearing from them. I rarely write someone who does not share a few details in their listing such as their hobbies and interests. However, I wrote someone last year having only their name and address. In my letter, I told them about myself – and said that if we don’t have much in common or you just don’t sense we’d be a good pen pal match – no problem and I will understand if I don’t hear back.

But even if I am writing a first letter to someone with whom I share similar interests, I will still say something like: You may or may not still be looking for new pen friends, but if you are, I will look forward to your letter.

#2  I also recently received a couple first letters from individuals wanting to be my pen pal – who got into rather controversial issues (politics) and said strong worded things about their political views and the views of people who think differently. Yes, no joke, in a first letter! I don’t think I have ever had this happen before in my many years of writing pen pals, and now it suddenly happens twice! Perhaps a reflection of the state of things here in the US at present.

By the way, I am not opposed to discussing “controversial” issues in letters as I have had interesting and beneficial dialogue with pen friends over the years – and it remained civil/friendly. However, broaching such issues depends on the situation and the particular pen pal. Wisdom is needed. At minimum, you should have established a friendship already, which takes time. It is definitely not appropriate in a first letter!

So…I just wanted to share those two things in light of recent letters I received. Don’t be demanding, expecting someone WILL write you back – and avoid controversial issues, at least in the beginning of a new pen friendship.

Quick tip – mention the date your pen pal wrote you

I’ve been an active postal pen pal for over 30 years. Years ago, I seemed better at remembering what I had already told a pen pal in my previous letter. Now I am not always so sure, and hate to repeat myself. Some pen pals are good at mentioning and responding to certain things you wrote about, as in “I enjoyed hearing about your hike at the state park.” – Okay, I told them about that already! – However, one does not usually make a comment about everything a pen pal wrote about.

A while back, I noted a couple of my pen pals would mention either the date at the top of my letter or the postmark date. I found this helpful, very helpful. If I wrote them on May 5th, I’ll know that I most likely shared key news up to that date – and will write about stuff that took place after that.

So, at some point, I started to begin my letters by mentioning the date of their letter. “I received your letter dated April 6th.”  – Hopefully, some of my pen pals find this helpful.

Years ago I knew a pen pal who kept a pen pal log book. Whenever she wrote someone a letter, she recorded the date and jotted down the topics she wrote about in the letter. Wow – for me – that would not work. Such record keeping would drive me mad! But we are all different and at least her penfriends did not get repeat news.


Are you making letter writing too difficult?

A problem sometimes encountered by pen pals is correspondents who write brief and superficial or monologue style letters. As an active pen pal for over 30 years, it is the most common complaint I’ve encountered among us. Most pen pals are looking for more, that is, letters that have substance and dialogue – where an actual friendship is being developed. I’ve blogged on this before. For example, see these posts:

A letter should be a dialogue, not a monologue 

Are you writing a friend, or only writing a letter?

While certain pen pals seem to put little effort or care into their letters, other pen pals may have the opposite problem! Are you making letter writing too difficult?

A few years ago I realized that somewhere along the line, as my years of writing progressed, that I had started making letter writing too complicated! I approached each letter almost like a project. I was overly concerned with including all my important news, and accurately describing things. I also over-thought my response to their letter, that is, what I should write in reply to what they shared with me. You might say that I developed perfectionist tendencies, wanting each letter to be “just right.”

As a result, I wasn’t enjoying writing to my pen pals as much as I used to in the past. Rather than being enjoyable, it had become more like a chore.

I realized that I needed to “chill” (relax) with my correspondence. My letters did not have to be perfect. That does not mean I began to write brief and superficial letters, but I became more casual with my approach. What 2 or 3 things from my life (instead of 5 or 6 things) did I want to share? If I didn’t describe something in enough detail or just right, that was okay. My pen pal could certainly ask me questions if they wanted to know more. Etc.

And… I began to enjoy my hobby again, the joy of maintaining friendships by mail.

I’ve encountered pen pals who, like me in the past, seem to have over-complicated their letter writing. Their letters are very involved and intense. These pen pals also take many months to write back, and state they have a hard time keeping up with their mail.

Maybe they are making it too hard? Maybe they are waiting until they can write a “perfect” letter? But sometimes you just need to pick up the pen and start writing.

On a related note, I find that waiting too long between letters can complicate things. Sitting down to write after 4 weeks, versus 6 months, is rather different. More time has gone by to consider and summarize, and leads to a more time-consuming letter to write. Of course, on occasion, there are legitimate reasons for a long delayed letter. Life happens, and sometimes letter writing must be disregarded for a time.

Again, I’m not encouraging superficial letters but maybe you need a more relaxed approach?

– Find a happy medium between a brief, superficial letter -and- a lengthy, overly thorough one.
– Make sure you are not procrastinating, waiting for the perfect time to write a perfect letter. Just start writing!

Where has all our time gone…for letter writing?

I self-published my own pen pal newsletter (print/by mail) for years, and then wrote a column for another such pen pal newsletter. Most of these newsletters ceased publishing, for various reasons. My point, however, is that I have written about many aspects of postal letter writing over the years and been active in pen pal circles. In this blog post, I am noting something that has changed…

It seems harder and harder to have pen pals that write regularly and consistently. An increasing number of pen pals only write 2-3 times a year. This is not a temporary thing, but long-term or the norm.

Flexibility is important with the pen pal hobby. We will all have times of life that are busier than others, and our letter writing may get delayed. Patience is a virtue. There is joy in receiving a long-delayed letter. I am thankful for pen pals that still keep in touch despite the ups, downs, and changes of life. Friendship is not about demanding someone keep a writing schedule!

With that clarification, what I am referring to is a pattern – it has become typical – for there to be excessive periods of time between letters.

In the past, I found that about 15 pen pals was “my limit” for me to be a consistent pen friend. More than about 15, I would have a hard time keeping up. I want to write quality letters and be a friend – not rushing through a letter just for the sake of answering it and getting mail. Back then, most pen pals wrote back fairly quickly, within 2-4 weeks. This kept my mailbox consistently happy – regular letters arriving in it!

But over the past 10 years or so, things have changed. In order to have regular letters arriving, I need more like 25 pen pals.

What is going on? I wonder…

Is it that the internet and cellphones have become pervasive? Time is consumed with these forms of communication – surfing the web, social media, texting – and postal letter writing is pushed to the side, even for pen pal enthusiasts?

A busyness epidemic has also taken over. A worthwhile article here: The Disease of Being Busy. Has this pervasive busyness likewise pushed postal letter writing to the side, even for pen pal enthusiasts?

I hope you might read the article I linked to above. Precisely because of our fast-paced and technological age, it is a good reason to get back into letter writing by post.

Slow down, thoughtfully reflect, pick up a pen, and share your life and thoughts with a friend by post. Not in a rushed way and not viewing it as a chore to be checked off a to-do list, but for your heart and soul. Take time for thought, dialogue, friendship.

No one wants to be viewed as a chore on a to-do list, and if that has become your approach (perhaps inadvertently) to writing letters to your pen friends, it is not too late for a re-boot (using a technological term!) – Make a fresh start with your letter writing.


Of course, I realize the incongruity of my writing this on a blog! It is not that technological is bad, but it should serve us and help us, not the other way around – where we can become a slave to technology.

Writing the first letter to a potential new pen friend

This is an edited version of a column I wrote a few years ago for the Inky Trail News. Inky Trails was a print pen pal newsletter, unfortunately no longer in print. Now-a-days I mostly find new pen friends through “friendship books” or a web site like Global Pen Friends. (Years ago there were more print based options.)

Writing the first letter to a potential new pen friend can be a challenge. In fact, I think some pen pals dread writing the first letter so much that they avoid doing it, even though they would really like some new correspondents. Instead they sit and wait for someone else to write first, but those letters may never come! To make new friends one must often be willing to take the initiative and reach out a hand of friendship. So I thought I would share some “first letter” tips in this issue’s column.

Those who regularly read my column know that I emphasize that a letter should be a dialogue not a monologue. Letters should not be entirely self-centered, only about you. Your pen friend should know that you are interested in them as well. You should respond to a letter with some comments or questions.

This applies to first letters too! You might be thinking, “But a first letter can’t be interactive. I have to tell them about myself, and I’ve never received a letter from them that I can respond too!”  – However, first letters can be interactive.

Likely you are responding to a pen pal ad/listing, and something about that listing appealed to you. What “jumped out at you” to make you willing to take the risk of writing the first letter? Let them know. Maybe you share some of the same interests. Maybe you are at the same “stage” of life. Maybe you just liked the style/attitude that came across in their listing. Respond and interact in regard to these things.

Mention what you have in common. “Your listing said you love reading. Me too.”  Share the genres you prefer, and ask them about their reading preferences.

The person likely has some interests that are different from you. Maybe one is something you know little about. Be interested and ask a question about it. “I noticed you like worldwide travel. I’ve never traveled outside the US. What countries have you been to? Do you have a favorite country?

Of course, a first letter will be lopsided towards you. That’s normal. And they need enough info to properly decide if they want to become your correspondent.

On that note, it can be hard to know how much to share in a first letter. I find the older I get, the harder it is to summarize myself! Where to begin? haha.

Just try to write enough that they can get a general idea about who you are. What are key things about you? What are the most important areas in your life? Details can be left for later letters. Remember that friendship takes time! So, don’t dump the whole load in the first letter.

Besides the challenge of writing a first letter, there is also the dread that the person will never reply. That happens. But try your best to inject at least a little conversation into the next first letter that you write. You may be more likely to receive a response! Best wishes making new friends on the inky trail!

Rubber stamped cards to match the USPS scratch-n-sniff popsicle stamps

I rubber stamped a set of cards to coordinate with the USPS scratch-n-sniff popsicle postage stamps. See the photo, for the cards and postage stamps. I’ll decorate the envelopes too. Note I am a simpler rubber stamper, and don’t like any stamping that is too complicated or time consuming. In these cards, some of the paper backgrounds are recycled – I will save a card or other random paper items if I think it would be good for paper layering.