Writing To Connect: 7 Simple Tips

Today I am delighted to be sharing a guest post by Hannah over at Holly Storman Art and Stationery, as she shares with us a few thoughts about putting pen to paper, a subject close to many of our hearts. Here she shares with us her musings around writing to connect with 7 simple tips. 

Learn how to write to deepen your sense of connection with others– both near and far

With the advent of social media and lightning fast internet, we are more interconnected than ever. However, at times it feels like the expansion of our ‘connectedness’ has come at the expense of the depth of those connections.  It’s easy to find ourselves keeping up with dozens of friends without feeling truly close to any of them!

Taking the time to slow down and rediscover some of the simple, timeless things that have always made life good, can help break this unfulfilling cycle, and old-fashioned letter writing is a great place to start!  Writing a letter, by hand, on a real piece of paper forces us to slow down, spend real time thinking about the other person, and savour the process itself!  

A text is as forgettable as it is convenient, and an email is just a small step above.  It’s the very fact that a letter takes more time and effort to produce – along with the deliciously delayed gratification involved – that makes it so much more satisfying and memorable.  

But considering most of us are out of the practice of slow and meaningful communication, it can be hard to know where to start!  That is where this guide comes in!     

Have you ever found a card or bit of stationery so perfect for a friend or loved that you can’t wait to send it to them to make their day… only to feel overwhelmed and intimidated by the task of actually writing something special and meaningful, the minute you sit down to write?  

I think we can all find ourselves there on occasion.  Soon enough five minutes have passed and we are still hovering our pen over the blank page, in indecision and frustration.  Until we inevitably abandon the project and promise ourselves, we’ll take it up tomorrow (sure bet!)  

The trouble is, we want so badly for our handwritten note to be something special that we put undue pressure on ourselves to write something amazing, often resulting in us not writing anything at all.  But it need not be that way!  

When we view our note writing as something akin to a school assignment, we’re missing the point – not to mention sucking the joy out of something that should be just as fulfilling and enjoyable for the sender as the receiver!  The point of course is connection – making someone you care about feel appreciated, seen, and loved.

And doing this is much easier than you think – that is if you’re willing to shed the writing assignment mentality and channel the true feelings and connection you share with that special person. You’ll find it can come quite naturally!

The reality is, any note written in you own hand, on a real piece of paper, delivered through the post, is special, no matter what it is you end up writing.  However, there are a few tips (7, in fact) that I will share with you here, that can spark your creativity, strengthen your connections with the one’s you love, and ultimately make letter writing a true joy!  

The first item on this list is the overarching starting point for all the others – and for fostering connection, more generally.  The remaining tips follow up with practical ideas and examples designed to get your creative juices flowing!


This may sound silly but it’s surprisingly easy to get so wrapped up in the task of writing that we kind of lose track of why we are writing at all – to connect with and delight the person we are writing to!  

I like to literally imagine myself as them, opening the card I sent them.  Are they going through something right now?  Are they likely distracted or worrying about something specific, that I’m aware of?  What is their day to day like?  Are they mind-numbingly busy or perhaps bored and lonely?  

These are excellent starting points!  What might they most like to hear right now?  What might be the greatest encouragement to them in this particular moment in time?  This is your starting point!

One of our deepest needs as human beings is to be seen and understood by those around us, thus real connection between two people is only ever formed through real understanding.  And delightfully, the benefits of taking the time to really understand another person don’t just go to the person being understood!  

Not only does it feel good to make someone else feel good, expanding our focus beyond ourselves, to see life through different eyes, is actually wonderfully freeing.  Incessant focus on ourselves and our needs is inherently restrictive, eventually narrowing our horizons down to a depressing pin point.  

Taking the time to view life through someone else’s eyes does exactly the opposite!  And real connectedness always enriches in both directions!  

Starting every letter or note with this simple exercise puts you in the other person’s frame of mind, allowing you to speak their language, immediately sparking a sense of connectedness by making them feel seen and perfectly understood!


So many of us, who are warm and engaging in real life, become stiff and formulaic in our writing, in an attempt to write “properly”.  But this is most certainly a mistake!  While grammar and writing conventions matter, these rules and guidelines should exist in the service of what you are trying to say, not the other way around!

Formality in writing has its place (resumes or an post-interview thank you note, perhaps) but that place is definitely not in a note meant to bring joy, and convey warm feelings, to someone you care about!  

When the main focus is on adhering to all the rules and regulations of proper writing convention it quickly gets in the way of genuinely expressing yourself in a way that feels personal… which is kind of the point, isn’t it!

This is not to say that you shouldn’t take the time to gather and order your thoughts before writing them down – you should!  But the end result should sound like you, not a grammar textbook.  

When your note reads so much like you, that the person reading it can easily hear your voice saying it in their head, it will instantly warm their heart and make them feel close to you, even though far away.  That’s what we’re going for!  

For Example:
If you would never say – “Our trip to the East Coast is currently planned for November, at which time we will be sure to reach out to you” than don’t write it in a letter to a loved one.
Instead, write it the way you would naturally say it –“We will be headed back east in November and will be sure to get a hold of you then!”

In short, say what you mean, in the way you would normally say it – in person – to that person!


When you are focused fully on the person you are writing to, anything you write them will be from the heart, but there are a few writing tricks that can really help communicate, in a deeper way, that you understand them and are truly interested in their life.

Simply asking a person how they are doing is certainly a good way to communicate interest in, and concern for that person but it is deficient in two ways.  Firstly, it is impersonal – there is nothing in that question that applies specifically to the person you’re writing to or even implies that you are taking the time to really think about them.  And secondly, the onus is entirely on the other person to come up with something interesting in response – they are being asked to do all the work!  

Instead, consider specifically what they might be feeling right now, or what their life looks like day to day, and ask questions that speak directly to these things.  When you’re able to put yourself in their shoes, as discussed in our first point, this can come quite easily!

For Example:

Instead of –“How is the new job? And are you enjoying having the kids home from college?”
Try –“I know you’ve been sorting through so many changes recently, with the new position at work and the kids unexpectedly home from college. I’m guessing things may feel a bit jarringly different right now!  How are you holding up?”


Just because you’re making an effort to really make the person you’re writing to feel seen and understood, doesn’t mean you shouldn’t share news from your life – of course you should! After all, that person also cares about you and your life and would likely love an update!  

You can certainly do this while still taking them fully into consideration.  It is, again, very simple and relates back to the first point of always viewing what you are writing through the eyes of the person you are writing to.

A few don’ts to keep in mind:

Don’t give a long, detailed account of something you have that you know the other person does not have – such as going on about your daughter’s acceptance into a top college when you know full well their son is struggling to finish high school.  

Don’t spend a lot of time sharing about a topic you know may trigger stressful feelings or bring up bad memories – if they have struggled to have children, don’t spend a lot of time gushing about your neighbour’s cute new baby.

But also a few do’s:

Do recount something you know they will find interesting and relatable!

Do share a recent event and relate it back to them by speculating on the ways they would have reacted to it or participated in it, had they been there.

For Example: 

Instead of –“Tommy lost his first tooth”

Try –“Tommy lost his first tooth last Thursday! And, just FYI, if you try to teach him that “spitting water through the tooth gap” thing you used to do as a kid, I will never speak to you again, haha!”

writing to pen pal


There is nothing quite like shared experiences to bond two people together! And reminiscing about these experiences is not only a way to actively strengthen that bond, it’s also a lot of fun!

We all love a good story – especially one that involves us!  But reminiscing doesn’t have to be reserved for fun experiences only.  Recounting an event or experience after the fact is how we make sense of our lives, so even a tough experience that wasn’t very enjoyable in the moment can become a great shared memory, depending on how you process it together!

For Example: 

  • Have fun with it! Make a joke about the expression on their face when you both found out you’d have to rent a car and drive the rest of the way to their sister’s wedding, two states away, after your flight was cancelled!  

Memories, are the little treasures that make up who we are – sharing them weaves us into the fabric of each other’s lives!       


There may be times when you just don’t have a lot to say but still want to show the other person you care and are thinking of them.  A wonderful quote is a great place to start!  Share the quote and describe to the person you love exactly why you love it and why it made you think of them.  

Not every letter or note you write need be a treatise to make an impact.  Sometimes sweet and simple is absolutely perfect and sharing a favorite quote is a great way to still make it special!   

For Example: 

  • Try something like this –“If you have good thoughts they will shine out of your face like sunbeams and you will always look lovely” ~ Roald Dahl” (One of my actual favorite quotes! )
  • And writing about how it makes you think of them need not be complicated either – “I saw this on the wall at the bookstore and it immediately made me think of you!  Missing your lovely face right about now… “

Letter written!  


This is not to imply that you are not sincere, because of course you are!  You wouldn’t be taking the time to write to someone you care about if you weren’t sincere.  

When I talk about sincerity, I’m referring to the difficult task of expressing our sincere feelings via the written word.  Sharing our true feelings always takes courage and vulnerability, no matter what the method, but it can feel extra challenging without the benefit of tone and facial expressions to add subtlety and nuance.

Because words on a page can feel very stark, it’s easy to overcompensate, by being too cutesy, over the top sappy, or even very stiff and distant, in our writing style, when it comes to expressing our feelings.  But the best rule of thumb is one that applies to all of life – just be sincere!  

Write exactly how you feel – no more no less – and don’t qualify or apologise.  Real feelings relayed in a sincere and straightforward way will never come off as sappy or juvenile and will always be respected and taken seriously.  

If you miss the person you’re writing to and wish you had spent more time with them when you had the chance, then tell them.  Your sincere vulnerability will likely inspire their trust and confidence as well, serving to deepen the connection you already have.  And that, after all, is why we write to each other to begin with, isn’t it!

I’m hoping you found this guide insightful, a fun read, and exactly the inspiration for letter writing that you were looking for!  I’d love to hear all the ways that you use the old-fashioned art of letter writing to connect to those you care about!  Viva la snail mail!

About Hannah

Hannah’s wearing the Snail Mail Forever tee, in the shop now!

Hannah Storman is a Blogger and Co-Owner of the Holly Storman Art & Stationery Co., as well as a mom and homemaker. In our modern world, that never seems to slows down, Hannah loves sharing ways to sort through all the noise and rediscover the simple, timeless things that have always made life good.

Follow along on Instagram, Facebook or her blog!   

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