Questions to Ask Your Friend's Boyfriend
Questions for the first few times you spend an evening with your friend's boyfriend, meant to get a real conversation going rather than an interview, with notes on where the friendly version tips over into interrogation.
The questions
Open any question for the note
How did you two actually meet? I have only heard their version.
Why ask it
A warm opener that gives him something easy and slightly flattering to answer. The two accounts rarely match exactly, and the parts he remembers that your friend left out are usually the endearing ones.
What was the first thing you noticed about them?
Why ask it
Better than asking what he likes about your friend, which invites a rehearsed answer. A specific first impression, something they said, the way they were standing, tells you he was paying attention.
What have they got you into that you would never have tried?
Why ask it
Reveals whether he treats your friend's interests as an intrusion or as a bonus. Someone who has been dragged to a climbing wall and enjoyed complaining about it is telling you something good.
What do you two do on a free Saturday with no plans?
Why ask it
The unstructured day is the honest one. Dates and holidays are performances; how a couple spends an empty afternoon shows how much they actually enjoy each other's company.
What have they told you about me that I should be worried about?
Why ask it
Disarming, funny, and it puts you in the exposed position rather than him. It also tells you whether your friend has been talking about their friends warmly or as material.
What do you do all day, and do you like it?
Why ask it
The second clause is what saves this from being a job interview question. People are far more interesting on whether they like their work than on what the work is.
What did you want to be when you were twelve?
Why ask it
Almost everyone enjoys this question and nobody feels examined by it. It also tends to produce the first genuinely unguarded answer of the evening.
What are you good at that nobody would guess?
Why ask it
Invites a small, specific boast rather than a summary of himself. Answers about odd skills or forgotten hobbies give the group something to come back to later in the night.
Where did you grow up, and how often do you go back?
Why ask it
The second half is more informative than the first. Frequency of return says something about family ties and about how rooted or unrooted his life currently is.
Who is the person you would call at two in the morning?
Why ask it
You are asking whether he has anyone, which matters, because a man whose only close relationship is his girlfriend puts all the weight of his life on her. A confident named answer is reassuring on its own.
What are you into that they do not get at all?
Why ask it
Healthy couples have separate enthusiasms and can describe them cheerfully. If he cannot name anything, either he has folded himself into the relationship or he is managing the answer for your benefit.
What is the best thing you can cook?
Why ask it
Low stakes and unexpectedly revealing about domestic life: who feeds whom, whether he does his share, whether he is proud of one dish or genuinely competent. It also usually leads to being cooked for eventually.
What is the longest you have gone without sleep, and why?
Why ask it
A story question rather than a fact question, and the reason is the interesting part. Answers range from work to travel to a night in a hospital corridor, any of which tells you more than a summary of his character would.
What is your worst habit, according to them?
Why ask it
Attributing it to your friend lets him be self deprecating without exposure. Watch whether he can laugh at himself, and whether the habit he reports is one your friend has actually mentioned to you.
What do they do that you find funny and have never told them?
Why ask it
This is the question that produces the most affectionate answer of the evening, because it asks for something he has noticed privately. Someone who has nothing here has not been watching closely.
What are you working towards at the moment?
Why ask it
Present tense and modest in scope, which gets a truer answer than asking about long term goals. It can be a qualification, a bike, a move, and any of those tell you where his attention goes.
What is the nicest thing anyone has done for you?
Why ask it
Shifts the conversation into warmer territory without it becoming heavy. The answer is often about a family member or an old friend, which fills in his life outside the relationship.
Where do you want to go that they have no interest in?
Why ask it
Playful, and it surfaces a real difference in an easy way. Listen for whether he describes the difference with amusement or with grievance, because that distinction matters.
What do the two of you disagree about and never resolve?
Why ask it
Every couple has a permanent low grade argument about the heating, the dishwasher, or being late. A cheerful answer means the relationship can hold a disagreement, which is more reassuring than a claim of never fighting.
What is something about them you think the rest of us miss?
Why ask it
A closing question that lets him say something generous, and it puts him on your friend's side rather than under examination. What he names also shows how well he actually sees them.
Meeting him without putting him on trial
Practical guidance for the conversation itself
Set the tone early
Say something warm in the first two minutes
He knows he is being assessed. Telling him your friend has been looking forward to this lowers his guard, and a relaxed person gives away far more than a defensive one.
Answer your own questions too
If you ask what he wanted to be at twelve, tell him yours. Trading beats extracting, and it stops the evening turning into a panel.
Do not run through a list
Three questions across an evening, with follow ups, is plenty. Anything more and he will notice the structure, and your friend will notice it before he does.
Include your friend in the conversation
Questions aimed only at him leave your friend sitting there being judged by proxy. The best material comes when they correct each other's version of a story.
Watch how he is, not only what he says
- Whether he lets your friend finish a sentence.
- Whether he speaks about their friends and family generously or dismissively.
- Whether he can be teased and can tease back without an edge.
- How he treats the waiter, the driver, or whoever else is doing a job around him.
- Whether your friend seems more themselves or less themselves when he is in the room.
- Whether anything he says about their relationship contradicts what you have already been told.
Where this goes wrong
Turning it into a screening interview
Questions about salary, prospects, and long term intentions on a first evening make you the problem rather than him. Those subjects are your friend's to raise, not yours.
Bringing up the ex
Comparisons are unfair to him and awkward for your friend, and once made they get repeated back later in an argument.
Reporting the whole conversation back
Your friend will ask what you thought. Answer that honestly and briefly, but avoid a line by line account that puts him under review every time he leaves the room.
Confusing dislike with concern
You may simply not click with him, which is not the same as him being bad for your friend. Keep those two judgements separate, in your own head first.
If something does worry you
Occasionally an evening produces something real: he corrects your friend constantly, he makes a joke at their expense that lands badly, he seems to know exactly where they are at all times. Do not raise it with him, and do not raise it with your friend as a verdict. Describe the specific thing you saw, once, without a conclusion attached, and say you are there whatever happens. People rarely leave a relationship because a friend disapproved, and they very often stop confiding in the friend who made it a condition.