There are two ways to get stuck on a letter. The first is having nothing to say, and we've written about that one already in what to write to a pen pal. The second is sneakier: you've told your news and signed off with love, then realized the whole letter is about you. You forgot to ask anything.
A question is the part of a letter that guarantees another letter. It hands your pen pal a thread to pull when they sit down to reply, and it tells them what you're curious about, which is its own kind of compliment. The letters that keep a correspondence alive for years are usually the ones that end with something the other person can't wait to answer.
So here are sixty questions, sorted roughly by how well you know each other, from first-letter openers to deep questions for a friendship with some years on it. The last ten are for restarting after a long silence. A word of advice before you start copying them out: two or three per letter is plenty. A letter with twelve questions reads like a customs form. Pick the ones you genuinely want answered, and when you can, answer them yourself in the same letter. A question offered with your own answer attached is a trade. A question on its own is an interview.
1–10 · For the first letters: getting acquainted
Early questions should be easy to answer and hard to answer boringly. These are that kind.
1
What does an ordinary Tuesday look like for you, from waking up to lights out?
2
What's the story behind your name? Who chose it, and was it almost something else?
3
What can you see from the window nearest to where you're sitting right now?
4
If I had one afternoon in your town, where would you take me first?
5
What made you want a pen pal in the first place?
6
What's a small thing you enjoyed this week that nobody else noticed?
7
Were you the front-row kid at school or the back-row kid? Or the one staring out the window?
8
What food could you eat every week for the rest of your life without getting tired of it?
9
What do you do with an hour that belongs to nobody but you?
10
Early bird or night owl, and has it ever been otherwise?
11–20 · Everyday life: the questions that keep letters warm
Once the introductions are done, a correspondence runs on ordinary days. Ask about them directly. People rarely get to talk about their Tuesdays, and most of them are quietly dying to.
11
What's honestly the first thing you do after waking up?
12
What's on your kitchen table at this exact moment?
13
Which household chore do you secretly not mind, and which one do you negotiate with?
14
What did you last cook that went wrong, and what did you end up eating instead?
15
Who did you last have a proper long conversation with, and what was it about?
16
What's your most-walked route, and what do you pass along the way?
17
What small purchase has improved your life completely out of proportion to its price?
18
What are you reading at the moment, and is it actually good?
19
What habit did you inherit from a parent without meaning to?
20
What sound do you hear so often at home that you've stopped hearing it?
21–32 · Deep questions, for a friendship with roots
Somewhere around the fourth or fifth exchange, one of you will risk a real question. It's the best moment in any correspondence. These work best offered gently, with your own answer included.
21
What smell takes you straight back to being small?
22
Whose kitchen do you remember best, and what was usually cooking in it?
23
What did you want to be when you were ten?
24
What's a piece of advice you're glad you ignored?
25
What have you changed your mind about in the last five years?
26
What comes easily to you that seems hard for everyone else?
27
When did you last feel properly rested, and what did that week look like?
28
Is there a friendship you miss? What would you write to them if you could?
29
What does "home" mean to you now, and has the answer moved over the years?
30
What were you worried about five years ago that turned out to be nothing?
31
What's the kindest thing a stranger has ever done for you?
32
What are you quietly proud of that never comes up in conversation?
33–42 · Just for fun: the letter equivalent of dessert
Not every letter needs depth. Some of the best ones are pure play.
33
What's your most defensible unpopular opinion? Food opinions count double.
34
If today were a chapter in a book, what would its title be?
35
What tiny, useless skill do you have?
36
Which fictional house would you move into tomorrow if you could?
37
House on fire, everyone safe, you can grab one sentimental thing. What is it?
38
What's the best meal you've ever eaten standing up?
39
What song do you put on when you're certain nobody is listening?
40
Is there a word in your language you love that doesn't translate properly?
41
If we swapped lives for one day, what must I absolutely not mess up?
42
What's the strangest compliment you've ever received?
43–47 · Seasons and places: letting the calendar help
A pen pal is a correspondent in another weather. Use that.
43
What does this season smell like where you live?
44
What's your favorite month? Defend it.
45
What's a tradition you keep even though nobody would notice if you stopped?
46
What kind of weather makes you want to sit down and write?
47
What's the first sign of the next season where you are, and has it appeared yet?
48–50 · About the letters themselves
The correspondence is allowed to talk about itself. These three tend to produce lovely answers.
48
Where do you read my letters, and where do you sit to write back?
49
Have you ever kept a letter for years? Who was it from?
50
What should I ask you more about?
51–60 · After a long silence: picking the thread back up
Every correspondence goes quiet at some point. That's a season, not a failure. The mistake is spending the whole first letter back on apology. Give the gap one honest line, then ask something that looks forward.
51
What's the headline from the months we didn't write?
52
What has changed in your ordinary day since your last letter?
53
Did the thing you mentioned in your last letter ever get resolved? I've been wondering.
54
What almost made you sit down and write to me, before life swept you off somewhere else?
55
What's on your table right now that wasn't there when we last wrote?
56
Who's been filling your days since we last wrote?
57
Is there something small you've been meaning to tell someone that never quite fit into a text?
58
If your last few months were a weather report, how would it read?
59
What went through your head when you saw my letter arrive?
60
Shall we pretend no time has passed, or do you want to tell me all of it? I'll take either.
How to actually use this list
Don't treat it as a syllabus. Read it the way you'd browse a shelf. Take the two or three questions that snag on something and leave the rest for another month. The list will still be here.
Remember the trade
"What smell takes you back to childhood?" is a nice question. "The smell of my grandmother's ironing takes me straight to 1999. What does it for you?" is a letter.
If you're the one holding the blank page today, our guide on what to write to a pen pal has thirty prompts for your own half of the exchange. And if you'd love letters like these arriving in your inbox on a schedule, written to you and waiting for your reply, that's the whole idea behind Penvelope. Fair warning about question 28: it's a hard one to answer dry-eyed.
Happy writing. Ask something real.