Questions to Ask a Married Man You Are Dating

The questions

Open any question to see why it works.

1. 1

   How would you describe your marriage right now, in plain words?

   The phrasing forces something concrete instead of a mood. Watch whether he describes a situation with facts in it, such as separate rooms or a filed petition, or only describes feelings, because those are two very different marriages.

2. 2

   Are you separated, and does that mean anything legal or only how it feels?

   Separated is used to mean everything from living in another apartment to sleeping badly in the same bed. Ask where he sleeps, whose name is on what, and whether anyone official knows, because the answer sets the timeline for everything else.

3. 3

   Does your wife know about me?

   This is the single most clarifying question available and it has only two real answers. If she does not know, everything he has told you about the state of the marriage is unverified, and you are the only one in this arrangement without full information.

4. 4

   Has this happened before?

   A pattern is different from a crisis. Ask directly whether there have been others during the marriage, because a man in one unhappy chapter and a man with a habit will describe the same present situation in the same words.

5. 5

   What do you actually want from me, in one sentence?

   Vagueness here is not shyness, it is a strategy, whether or not he knows it. Push until you get something you could repeat to a friend without translating it, and notice if he answers with how he feels about you instead.

6. 6

   What do you think happens next, month by month?

   Ask him to lay out an actual sequence with dates in it. Most answers collapse into someday, and the collapse tells you more than the words did.

7. 7

   What would have to be true for you to leave?

   You are listening for conditions that can actually occur. When the children are older, when work calms down, when she is stronger are all conditions with no fixed date, which means they are reasons rather than plans.

8. 8

   Have you said any of this to her?

   Whatever he tells you about his marriage being over is a claim until it has been said to the person he is married to. Ask when, in what words, and what she said back.

9. 9

   Are you in counselling with her, or trying to fix it?

   Men in this situation sometimes run repair and escape at the same time, and both women are told they are the plan. Ask what the counselling is for and what he tells the counsellor about you.

10. 10

    Who else knows about us, and how do I appear on your phone?

    The practical answers reveal how you are categorised: a false name, a locked device, friends who have never heard of you. Being a secret has costs that do not show up until something goes wrong and there is nobody you can call.

11. 11

    What do you expect me to do at weekends and on holidays?

    This is the part people skip until it hurts. Ask specifically about birthdays, Christmas, holidays, illness, and what happens if you need someone at two in the morning.

12. 12

    If your wife walked in tomorrow, what would you do first?

    The order of his answer is the answer. Notice whether protecting the marriage, protecting you, or protecting himself comes first, and whether you appear in the plan at all.

13. 13

    What have you promised her that you have also promised me?

    People in this position often say the same sentences in two houses. Asking about it plainly is uncomfortable and it is the fastest way to find out how much of what you have been told is specific to you.

14. 14

    If there are children, what happens to them if you leave?

    Custody, housing and money are the practical machinery of any divorce, and they slow everything down. A man who has thought about it can describe the arrangement; a man who has not is not as close to leaving as he says.

15. 15

    Have you spoken to a lawyer, and do you know what a divorce would cost you?

    This is the most reliable test of intent in the whole list. Intending to leave and having taken a single concrete step toward leaving are separated by one phone call, and many people never make it.

16. 16

    What are you risking here, and what am I risking?

    Ask him to name both columns out loud. The imbalance is usually obvious once it is spoken, and his willingness to say it is itself information about how honest this is going to be.

17. 17

    What would you tell someone you love if they were in my position?

    Most people are much clearer about other people's situations than their own. His answer will often be the truest thing he says all evening, and it is worth sitting quietly afterwards rather than filling the silence.

18. 18

    If nothing changed for two years, would you still want this arrangement?

    Removing the promise of change from the question is what makes it useful. If the honest answer is yes, then this is not a transition, it is the shape of the thing, and you can decide about it as it is.

19. 19

    If she asked you to end this today, would you?

    Ask it flatly and watch the pause before the words. Hesitation is not cruelty, it is the actual answer arriving before the polite one does.

20. 20

    What do you think I deserve?

    This ends the conversation on the only question that is really about you. A man who cannot answer it, or who answers it with reassurance about his own feelings, has told you where you sit in his life.