Questions to Ask Daughter's New Boyfriend
Questions for the first few times you meet the young man your daughter is seeing: light enough for a nervous guest, specific enough that you finish the evening knowing something real about him.
The questions
Open any question for the note
What should we call you?
Why ask it
A small question that settles a surprising amount, since plenty of people go by a middle name, a shortened one or a nickname their family never uses. Asking also signals that you are not going to guess at things about him.
How long have you two been seeing each other?
Why ask it
Worth asking him rather than her, because the two answers sometimes start from different events. A noticeable gap is not a scandal, but it tells you they have not compared notes on what this is.
Where did you grow up?
Why ask it
Gives him a subject he cannot get wrong, and place names usually pull other details along with them: a school, a move, a parent's job, how far he is from home now.
What are you up to these days, school, work, or both?
Why ask it
Deliberately open, so he can answer honestly if the truthful answer is "neither at the moment." How he handles an unimpressive answer often matters more than the answer.
What does a free Saturday look like for you?
Why ask it
More revealing than a list of hobbies, because it captures what he actually does rather than what he would like to be known for. Notice whether anyone else is in the picture.
What have you gotten into lately, a game, a show, a sport?
Why ask it
Lets a shy young man talk at length about something safe, which is often the point of the first meeting. You are watching whether he can hold a conversation, not auditing his taste.
Who are the people you're closest to?
Why ask it
The answer maps his support system. A couple of friends and a sibling is healthy. If the list is only your daughter, expect her to be carrying more than she has mentioned.
What's your house like, loud or quiet?
Why ask it
An easier way in than asking about his family directly, and it tends to produce the honest version: who cooks, who argues, who is never home. Compare it to the house he is now sitting in.
What made you want to ask her out?
Why ask it
You want a reason with a detail in it, something she said or did. Answers about how she looks, or that she was the one who did the asking and he simply went along, are worth noting quietly.
What did she tell you about us before tonight?
Why ask it
Usually gets a laugh, and it shows you two things: how your daughter describes her family to someone new, and whether he arrived braced for something.
What do the two of you end up talking about most?
Why ask it
Couples with a shared subject, music, a class, a game, siblings, have something to do besides be a couple. If nothing comes to mind, the relationship may still be mostly proximity.
Is there anything coming up this year you're looking forward to?
Why ask it
Gentler than asking about his plans, and it surfaces what he is organising his time around: a season, an exam, a trip, a move. Whether your daughter appears is worth hearing.
What's something you're stubborn about?
Why ask it
People answer this more honestly than they answer questions about their flaws, and it shows you where he will not bend. A funny answer still counts, so long as it is specific.
Is there something you've stuck with for a long time?
Why ask it
Years of an instrument, a team, a part-time job or caring for a grandparent all say something no plan can: he can keep going after the novelty wears off.
How do you get around, do you drive?
Why ask it
A practical question with real weight for a parent, since it decides how your daughter gets home at midnight. Ask who else is usually in the car and how far they tend to go.
When plans change at the last minute, how do you two let each other know?
Why ask it
Small logistics reveal habits: whether he answers his phone, whether either of them expects instant replies, whether she is the only one apologising for being late.
When you and your friends disagree, how does it usually settle?
Why ask it
Asking about friends rather than about her gets a less rehearsed answer. Listen for whether disagreements end in a conversation, a sulk, or someone being cut off.
What's something about you that isn't obvious right away?
Why ask it
Hands him control of the introduction, which is a kindness on a first visit. It also often produces the one detail you remember a month later.
Where do you think you'll be a year from now?
Why ask it
Short enough a horizon that he has to answer with something real. Vagueness at eighteen is normal, but notice whether the answer is his own or an inherited plan he has not questioned.
Anything you want to ask us, or about how things work around here?
Why ask it
Closes the meeting as a two-way exchange and gives you a natural place to state house rules once, calmly, rather than as a warning later on.
The first few meetings
Practical guidance for the conversation itself
Making the first visit survivable
Keep it short and give it an end
An hour with a stated finish, dinner and then they are going out, is easier on everyone than an open evening. Nobody has to work out when the interview is over.
Let someone else be in the room
A sibling, a second parent, a dog. Three or four people in a kitchen produce ordinary conversation. One adult across a table from one teenager produces a hearing.
Ask your daughter what to avoid
Not what to ask, what to avoid. A dead parent, a job he just lost, a family situation he is embarrassed about. Two minutes with her beforehand saves an awkward ten minutes later.
What a first meeting can and cannot tell you
Not much about his character yet
First impressions with a girlfriend's parents mostly measure nerve. Quiet, over-polite, awkwardly formal and slightly boastful are all normal on a first visit and often gone by the third.
Quite a lot about his manners
Whether he greets everyone, thanks whoever cooked, takes his phone out mid-sentence or talks over your daughter. These are habits rather than nerves, and they show up straight away.
Almost everything about how he treats her in front of you
Watch the small exchanges, not the answers to your questions. Whether he lets her finish, whether he corrects her, whether he checks in with her before answering for both of them.
Questions to hold back for now
Marriage, children and money
On a first meeting these read as either a threat or a joke, and the answers are worthless in both cases. They are reasonable questions a year in, when there is something to answer about.
Religion, politics and previous girlfriends
Each one invites him to guess the answer you want. If any of these genuinely matter to your family, they will come up more honestly in the ordinary course of him being around.
Anything phrased as a test
"So what are your intentions?" tells him the conversation is a performance, and from then on that is what you will get. The same information arrives on its own if he keeps coming back.
After he leaves
Give your daughter something positive first
One true, specific thing you liked about him. It costs nothing and keeps her willing to tell you about him next time, which is the only real source of information you have.
Save concerns for a separate conversation
Delivered in the same breath as the compliment, a concern is all she will hear. Wait a day, name the behaviour rather than the boy, and say it once.
Invite him back before you've made up your mind
A second visit is where you learn the things a first visit hides, and the invitation itself tells your daughter you are not looking for reasons to disapprove.