Questions to Ask Your Inmate Boyfriend

The questions

Open any question to see why it works.

1. 1

   What did today actually look like, hour by hour?

   Days inside are highly structured and almost never described in letters, so both of you end up guessing at each other's ordinary hours. Asking for the timetable gives you something concrete to picture and gives him something easy to answer on a bad day.

2. 2

   What was the best thing that happened this week?

   Deliberately small. If the honest answer is that nothing good happened, that is useful information about where he is, and it is easier to admit to this question than to a direct one about his mood.

3. 3

   Who do you talk to in there, and who do you keep away from?

   You will hear the same handful of names for months, so learning them early makes every later call shorter and clearer. He may keep the second half of the answer vague, and pushing on it in a monitored call is not fair to him.

4. 4

   What do you do with the hours nobody schedules for you?

   Unstructured time is where the difficulty lives. Someone who has built a routine into it, reading, drawing, working out, letters, is doing better than someone who describes the same hours as waiting.

5. 5

   What are you reading or watching?

   One of the few subjects where you are on level ground, and it gives you something to do together at a distance. Reading the same book and talking about it turns a call into a conversation rather than a status report.

6. 6

   What is the food like, and what do you miss eating?

   A light question that gets a real answer. The thing he misses eating is worth remembering for the first meal after release, and it often comes with a memory attached.

7. 7

   Is there a job, class or program you can get into, and what is the waiting list like?

   Access varies enormously between facilities and is often gated by a waiting list or by conduct. Knowing what he is trying to get into gives you something to ask about across months rather than a single conversation.

8. 8

   What can I actually send, and what gets rejected?

   Mail rules differ by facility, change without notice, and often cover things that surprise people: photographs, stamps, printed pages, anything in colour. Ask him to read you the current list rather than guessing, since a rejected package can cost you both a review.

9. 9

   How much do calls and messages cost you, and how many do you get?

   Talk about it plainly rather than letting it become a silent resentment about who called and who did not. Once you both know the limit, you can decide together which days matter most instead of spending it all in the first week.

10. 10

    What day and time works best for a visit, and what should I know before I come?

    Visits have booking windows, identification requirements and dress codes, and people are turned away over small things. Ask him to walk you through it once, in detail, and write it down.

11. 11

    What do you want me to tell people who ask about you?

    This spares you improvising an answer to his mother, your coworker and a stranger in the same week. It also tells you how much of his situation he considers yours to share, which is a boundary worth having explicitly.

12. 12

    What do you want to hear about my life out here, and what makes it worse?

    Some people want every detail of the outside world and some find it unbearable. Assuming the wrong one leads to letters that hurt him or letters that feel like you are hiding your life.

13. 13

    When you are having a bad day in there, what do you actually want from me?

    The choices are roughly: talk about it, distract me, or just stay on the line. Getting this settled in advance stops you offering comfort in a form he cannot use during a call with a clock running.

14. 14

    What are you afraid I am doing out here?

    Distance breeds a specific kind of suspicion in both directions, and it usually goes unnamed until it comes out sideways in an argument. Asking directly lets him say it once, in daylight, rather than circling it for months.

15. 15

    What has changed about how you see the last few years?

    Long stretches of time with little to do produce a lot of revisiting. The answer tells you whether he is reckoning with what happened or building a story in which nothing was his, and that difference matters more than any promise about the future.

16. 16

    What do you think will be hard about being out that nobody warns people about?

    Reentry catches people on ordinary things: crowds, decisions, phones, being alone in a room. Someone who has thought about it in that register is planning; someone who describes release as pure relief has not started yet.

17. 17

    Where would you live in the first month, and who is on that list besides me?

    Housing is usually the first thing that has to be arranged and often has conditions attached to it. If your name is the only name, that is a conversation to have now rather than the week before he walks out.

18. 18

    What are the conditions after release, and what happens if one gets broken?

    Supervision terms can cover work, travel, curfew, contacts and where he is allowed to be. You need to know the practical shape of them because they will shape your life too, and neither of you should be finding out by accident.

19. 19

    What do you want the first ordinary day together to look like?

    Not the first hour, the first ordinary day. It moves the conversation off the fantasy of the release date and onto something you can both actually picture, and it usually surfaces a mismatch in expectations early.

20. 20

    What do you need from me right now that you have not asked for?

    Ask it at the end of a good call, not a hard one. People in this situation get careful about asking, especially for money or time, and the unasked thing is generally the one causing the strain.