Pen Pals Later in Life, for Retirees and Older Writers

If you were writing letters before email existed, you may have noticed something odd. The skill everyone else is now trying to learn, how to write a long and thoughtful letter to a stranger, is one you already have.

Correspondence suits the later decades of life very well. Here is why, and how to get the most out of it.

Why letters suit this stage of life

There is time to write properly. A good letter takes an hour or so, and most people in the middle of their working lives do not have that hour. If you are retired, you may well have it. You can draft on Monday, reread on Tuesday and send on Wednesday. Letters written like that are a pleasure to receive, and your pen pal will notice.

You have material. Decades of work, places, people, changes and opinions. A twenty-five-year-old pen pal in another country has never seen your world, and much of what feels ordinary to you will be new to them.

It brings back a routine. Retirement can take away the structure of the week. Writing on a fixed morning, with the post or the inbox as a reason to sit down, gives some of it back.

Writing across generations

Some of the best correspondences are between people thirty or forty years apart. Neither person is competing with the other, and each has something the other cannot easily get anywhere else.

One practical note first: PenPalConnect keeps under-18s completely separate from adults, so as an adult member you will be writing to other adults. "Younger" here means someone in their twenties or thirties, not a teenager.

Writing to younger pen pals

A few things help:

• Ask about their life as it is now, not just as it compares to yours. "What does a normal working day look like for you?" works much better than "in my day we...". You will get to tell your stories. Let them ask.
• Do not hand out advice unless it is asked for. It is very tempting, and it nearly always lands as a lecture. If they bring up a problem, ask what they are thinking of doing before saying what you would do.
• Be curious about their technology and their slang. Being honestly baffled by something, with good humour, is endearing. Being dismissive is not.
• Tell them what was different, plainly. What a phone call abroad used to involve, what you did on a Saturday at their age, what things cost. Younger people often find this fascinating, as long as it is told as a story and not as a comparison they are losing.

Writing to peers

Writing to someone your own age in another country is a different pleasure. You lived through the same decades from different sides. Where were you when the big news stories of your youth broke? What did your parents think of the music you liked? How does retirement work where they live: the age, the pension system, whether grandparents do the childcare?

These letters can go deep quickly, because you share a reference point.

The technology, gently

You do not need to be good with computers to have a pen pal online. You do need a setup that is comfortable.

Make the text bigger. On most computers, holding Ctrl (or Cmd on a Mac) and pressing the plus key enlarges everything on the page. Phones and tablets have a text size option in their settings. There is no prize for squinting.

Type on a proper keyboard if you can. Writing a long letter on a phone screen is tiring for anyone. A tablet with a cheap plug-in keyboard, or an ordinary computer, makes a real difference.

Draft somewhere else if that is easier. Write by hand or in a word processor, then copy the finished letter across, so nothing is lost halfway through.

Ask a family member to set it up once, then do it yourself. Having someone sit with you for twenty minutes to show you the basics is sensible. Having them write your letters is not. Your pen pal wants to hear from you.

About handwriting. If you love writing by hand, keep at it. Draft by hand, or, once you trust a pen pal, swap the occasional postcard. A photograph of a handwritten page attached to a letter can also be a lovely touch. Before anything goes by post, though, read the safety section below about addresses.

What to write about when you have decades of stories

Here is the odd problem with a long life: too much material. The temptation is to summarise, "I worked as an engineer for thirty-five years, married, three children, moved twice", and a summary is the least interesting thing you can send.

Pick small stories, not your whole life. Not "my career", but the first day at that job and what you got wrong. Not "my childhood", but the kitchen of the house you grew up in, and who was usually standing in it. One room, one afternoon, one person. The larger story comes through on its own.

Let their letter decide which story. If they mention starting a new job, that is your cue for the new-job story. If they mention their grandmother's cooking, tell them about yours. Stories that answer something they said feel like conversation. Stories that arrive unprompted feel like a memoir.

One story per letter. Keep the others. You have plenty, and holding some back keeps you interesting for years.

Write about now as well. The garden, the book you are reading, the grandchild who has learned to say "actually". It stops the letters becoming a museum.

If you get stuck, the list in what to write about has plenty of starting points.

Safety: the bit that matters most

This is not meant to alarm you, but scammers do deliberately target older people on pen pal and dating sites.

The two patterns to know:

The romance scam. Someone writes warmly and often, very quickly says they feel a special connection, and is usually working somewhere far away: an oil rig, a military posting, a ship, a medical mission. Over weeks the letters build up to a problem: a frozen bank account, a medical bill, a customs fee, a plane ticket to come and finally meet you. The amounts start small.

The money or investment story. Someone friendly mentions, casually, how well an investment, often a cryptocurrency platform, has done for them, and offers to show you how. It feels like a favour from a friend. It is not.

The rules are simple and do not bend:

• Never send money, gift cards, or bank or card details to anyone you met online. Not for an emergency, not as a loan, not once.
• Be wary of anyone who wants to move quickly to WhatsApp, email or phone. Moving you off the site is often the first step, because it takes you away from the reporting tools.
• Do not share your home address, phone number or full name early. Wait until you have exchanged many letters and are sure, and even then think about whether you need to.
• If something feels off, tell someone you trust before replying. Scams depend on secrecy.

Real pen pals never ask for money. Not "not usually": never. There is a fuller list of warning signs in pen pal scams: the red flags, and it is worth ten minutes before you start. The safety page covers what to do if something feels wrong, and a pen pal who has verified on video is at least who their photos say they are.

Start with one letter

Write a short first letter that says who you are now, not your CV. Mention one thing you are enjoying and ask one question about their life.

Write your first letter →