Getting to know someone through letters is slower than a first date and, done well, deeper. You have time to ask properly and she has time to answer properly. The mistake most men make is not asking bad questions but asking the right questions too early, or asking three at once, or asking without offering anything of their own. This article puts the questions in order.
What makes a question work in a letter?
- It has an easy first answer. "What does a normal Tuesday look like?" can be answered in two lines or twenty. "What are your values?" cannot be answered at all before lunch.
- It comes with your own answer. If you ask about her morning, describe yours first. She then knows the register you are writing in and does not feel interrogated.
- It is one question. Three questions in one letter get one answer, usually to the easiest. Save the others.
- It survives a language gap. Most letters here cross one. Concrete questions come back as her; abstract ones come back as a paragraph that could be anyone's.
- It is not a test. A question asked to check her against a list ("do you want children?", "would you move?") in the second letter reads exactly as what it is.
Questions for the first two or three letters: her ordinary life
These are low-stakes, easy to answer, and tell you more than they appear to.
- What does a good weekend look like for you, and what does the usual one look like?
- What is the first thing you do in the morning, and the last thing at night?
- Where do you go in your city when you want to think?
- What is the meal you cook when you cannot be bothered, and the one you cook when someone matters?
- What is a small thing that made this week better?
- What did you want to be at twelve, and how close did you get?
Remember the time difference when you read her answers. Kyiv is seven hours ahead of New York; "I am writing this before work" means her morning is your night, and a letter that arrives at three in the afternoon your time was probably written at ten in the evening hers, after a full day.
Questions about family and the past: how and when to ask
Family is a good subject from about the third letter on, if you lead with your own. "My father was a bus driver who never once complained, and I am still trying to live up to it. Who in your family are you most like?" opens the door without pushing her through it.
- Who in your family do you speak to most often, and what about?
- Is there a family tradition you kept, and one you were glad to drop?
- Do you have children? What are they like, and what do they think of your cooking?
Her previous relationships are hers to raise. If she mentions a marriage or a former partner, you can ask a gentle follow-up ("how long ago was that?"), but do not ask why it ended, and do not ask the question that sits under a great deal of bad online-dating advice: "why is a woman like you single?" It has no good answer and she has heard it before.
Some of her family may be in the army, abroad, or in a part of the country she does not want to talk about. If she goes quiet on a family question, change the subject without comment. She will come back to it, or not, and either is her right.
Questions about what she wants: relocation, children, timing
These are the questions men most want to ask and should ask last. They are legitimate; a man of fifty-eight thinking about a relationship with a woman in another country needs to know whether she would move, whether she wants children, how she sees the next few years. But asked in the second letter they sound like a job interview, and asked before you have seen each other on video they are answered in the abstract, to a stranger. Ask them after two or three video calls, when she knows whose question it is.
- When you imagine life in five years, where are you, and who is nearby?
- Have you lived anywhere other than where you are now? What did you miss?
- What would be hard for you about leaving, if you ever did?
- Do you want children, or more children? (Only once she has spoken about family herself.)
Ask them one at a time, with your own answer alongside. "I am not moving to Kyiv, I have a business and grandchildren here, so I want to be honest that this is a question about you coming here one day. Is that something you have thought about, and what worries you about it?" is direct without being cold.
Fun questions, deeper questions, and questions that show you listened
Three short lists, for when the ordinary-life questions have done their work and you want a change of tone without a change of subject.
Fun questions
- What is the one dish you would never let anyone else cook for you?
- Which was the worst haircut of your life, and who was responsible?
- If you had a free Saturday and a full tank of petrol, where would you drive?
- What is the song you know all the words to and would deny knowing?
Deeper questions, from the fifth or sixth letter on
- What is something you changed your mind about in the last few years?
- Who taught you the thing you are best at?
- What does a calm life look like to you, in practical terms — a place, a rhythm, a person?
- What is a small promise you have kept for a long time?
Questions that show you read her letters
- You said your mother taught you to bake; does she still tell you what you are doing wrong?
- Last week you were dreading a meeting; how did it go?
- You mentioned the park near your flat — is it the kind with benches and old men playing chess, or the kind with a lake?
Every question here still follows the rule at the top of this page: one at a time, your own answer first. The third list gets the longest replies, because it is built from her words rather than from ours.
Questions about language
It is entirely fair to ask how much English she has. Ask plainly and without suspicion: "How is your English — should I keep my letters simple? I ask only because I would like to know how you would prefer to speak when we get to a video call." Whatever the answer, the thoughts are hers, and the surest way to hear her own voice is a short call; the video dating page explains how to handle the language on a call.
Questions to save for video, and questions never to ask
Save for video: anything about the future you share, anything about health, anything where tone matters more than words. A ten-minute call answers these better than ten letters.
Never ask in letters:
- What the war is like, whether she is afraid, what she has seen. She lives inside it; she does not owe you a description.
- Anything about money: her salary, her rent, what things cost, whether she needs anything. The site has no way for members to send each other money, and the safety guide explains why a conversation that turns to money is one to step back from, whoever started it.
- Anything sexual, in any wording, at any stage of the letters.
- Anything that begins "why don't you just".
How to answer your own questions
A letter that asks and does not answer is an interview. Write your answer first, in the same length you hope for from her, then ask. If you ask what she cooks when someone matters, tell her that yours is a roast that takes all afternoon and that your daughters rate it seven out of ten. That sentence tells her your age, your family, your humour and your kitchen, and she will answer in the same spirit. The article on conversation starters has more examples in this shape.
What to do next
Pick one question from the first list, write your own answer to it, and send it as your next letter. When you have exchanged four or five letters each way and the answers are getting longer, suggest a short video call inside the site; the first video date article covers what to talk about when you get there. If you are still choosing whom to write to, the members gallery is open without an account.