Funny Questions to Ask Your Daughter's Boyfriend
Twenty light questions to ask your daughter's boyfriend the first few times he comes over, meant to keep dinner relaxed rather than put him on trial: the useless superpower he would pick, the food combination he defends, and the worst thing he has ever cooked.
The questions
Open any question for the note
What's the weirdest food combination you'll defend to anyone?
Why ask it
A safe first question because there is no answer that can make him look bad. It also tells you what he grew up eating, which is a friendlier route into his family than asking about it directly.
If you were a kitchen appliance, which one would you be?
Why ask it
Silly enough that he can see it is not a test. The tell is whether he plays along or stalls, which tells you how nervous he actually is rather than how nervous he looks.
What's the worst thing you've ever cooked?
Why ask it
Cooking disasters are self-deprecating without being personal, so this is where a guarded guest usually relaxes first. Follow up by admitting yours.
If you could pick one superpower, but it had to be completely useless, what would it be?
Why ask it
The constraint blocks the rehearsed answer about flying or time travel and forces something invented on the spot, which is where his actual sense of humor shows up.
What's the weirdest talent you have that nobody would guess?
Why ask it
Most people have one strange party trick. If he says he has none, ask what he was into at fourteen, since that is usually where the odd skill came from.
What's the most embarrassing song you'd never skip?
Why ask it
A small, cheap confession that costs him nothing. If he names something obviously cool, he is still managing his image and needs another few questions before anything real arrives.
What's the strangest thing you've ever googled?
Why ask it
Expect an edited answer, and that is fine. The reason behind the search is usually funnier than the search, so ask why he needed to know.
What's the most embarrassing thing that happened to you at school?
Why ask it
School is far enough in the past to be safe territory. Middle school specifically works better than high school, because the stories are more absurd and less raw.
What's a ridiculous fear you'll admit to?
Why ask it
Framing it as a fear he will admit to, rather than one he has, leaves him an exit if he needs one. If he offers a real one, do not analyze it, just laugh and offer your own.
If you had to describe yourself with three film titles, which would you pick?
Why ask it
This gets you his self-image sideways rather than head-on. Watch whether the three titles agree with each other, because the mismatch is usually the honest part.
What's the most ridiculous thing you've done to avoid a job you didn't want to do?
Why ask it
Procrastination stories are universally relatable and mildly incriminating, which is the right level for a first dinner. Nobody has ever been judged for this one.
If you could be famous for something completely pointless, what would it be?
Why ask it
Absurd by design, so a flat answer here usually means he is still trying to give the correct response rather than a funny one. Give him a bad example of your own and try again.
What's a hill you'll die on that genuinely does not matter?
Why ask it
This is where people get animated without getting personal, and a dinner table argument about pineapple or thermostats is the best possible outcome of the evening.
If you had one day in any job at all, what would you spend it doing?
Why ask it
One day keeps it playful rather than an interview about his career plans. If he names something wildly impractical, that is a better sign than a rehearsed ambition.
What's the most ridiculous thing you've done to impress someone?
Why ask it
He will probably choose a story about a friend rather than about your daughter, which is the tactful move and worth respecting. Do not steer it back.
What's the strangest thing you've ever convinced someone was true?
Why ask it
Reveals whether his humor runs to gentle nonsense or to something with a victim, which is genuinely useful information delivered as a joke.
If you were stuck somewhere for a month with three objects, what would you bring?
Why ask it
Watch whether he goes practical, sentimental or entirely silly. All three are fine answers, but they are three quite different people.
What's the funniest thing your family does that you assumed everyone did?
Why ask it
A warmer route into his background than asking what his parents do for a living, and it usually produces a tradition worth stealing.
What would your friends say is your most annoying habit?
Why ask it
Routing it through his friends makes self-criticism easy, and the answer is more honest than anything he would volunteer about himself.
What did you expect this dinner to be like before you got here?
Why ask it
Best saved for the end, once he is comfortable enough to be honest. It usually gets a laugh and quietly acknowledges that the evening was nerve-racking for him.
How to keep a first dinner relaxed
Practical guidance for the conversation itself
Before he arrives
Ask your daughter what is off-limits
Two minutes beforehand saves the whole evening. She will know whether his parents are divorced, whether he lost a job recently, or whether there is a subject he flinches at. You cannot guess these.
Give the meal a job
Cooking together, a card game or a dog to walk gives everyone something to do besides look at each other. Sitting across a formal table doubles the pressure on him for no benefit.
Decide not to interview him
He is expecting questions about grades, plans and intentions. Not asking any of them in the first hour is the single most effective thing you can do, and the questions above exist to fill that hour.
During the conversation
- Answer each question yourself before or after he does, so it reads as a game rather than a screening.
- If he gives a one-line answer, follow with how old were you rather than repeating the question.
- Let your daughter interrupt and contradict him. Her joining in is what makes him stop performing.
- Notice whether he asks anything back. That is more informative than any answer he gives.
- End it while it is still going well. Twenty questions is a list to choose from, not a script to finish.
What to avoid
Jokes about his intentions
The shotgun line, the where are you taking her line, the you know I know people line. He has heard them, he cannot respond to them, and every one of them tells him the light questions were a warm-up.
Making your daughter the subject
Questions that ask him to rank, rate or evaluate her put him in an unwinnable spot and embarrass her at the same time. Keep him as the subject and her as a participant.
Treating a nervous answer as a character flaw
A dull answer to a silly question usually means he is anxious, not humorless. Judge him on the second half of the evening rather than the first ten minutes.