Funny Questions to Ask Future Son-in-Law
Twenty light questions for a future son-in-law over dinner or at a holiday gathering. They cover what he expected your family to be like, the meal he ruined trying to impress your child, what he is unreasonably competitive about, and what he is dreading about the wedding.
The questions
Open any question for the note
What did you think our family was going to be like before you met us?
Why ask it
A good opener because it lets him be funny about his own expectations rather than about anyone present. Whatever he braced for tells you what his own family is like.
What's the worst first impression you've ever made on anyone?
Why ask it
Deliberately not about you, so he can tell a story without calculating who is listening. If he tells one about meeting you, he is more relaxed than he looks.
What's a meal you cooked to impress your partner that did not survive?
Why ask it
Kitchen disasters are the safest funny territory in a first real conversation, because the only casualty was dinner. Ask what they ended up eating instead.
How long did you wait before you told your friends about them?
Why ask it
The number is the joke, and the answer is usually either the same night or a suspiciously long delay with a reason attached. Either version comes with a story worth hearing.
What's the most ridiculous thing you did early on to seem more impressive than you were?
Why ask it
Invites him to expose himself first, which is what most people in his position are hoping for. Feigning an interest in a sport or a cuisine is the usual answer.
Which of your own family stories don't we know yet?
Why ask it
Signals that you want him to have a family rather than to have joined yours. The story he picks is the one his family tells at every gathering, so you will hear it again.
What's a rule in your family that we're going to find strange?
Why ask it
One of the best questions here, because every household has one and nobody notices their own. Shoes, seating, who carves and when presents get opened are where the answers cluster.
What are you unreasonably competitive about, so we know before game night?
Why ask it
Practical intelligence disguised as a joke. If he denies being competitive about anything, ask his partner, and enjoy what happens next.
What food are you going to have to pretend to like in this house?
Why ask it
Funny and genuinely useful, since somebody has been serving him something he does not eat. The braver the answer, the more comfortable he actually feels.
What's the worst gift you've ever given someone you were trying to impress?
Why ask it
Keeps the embarrassment historical and safely distant from any gift he has given you. The good answers involve a size, a scent or an appliance.
What did you think the first time you saw where your partner grew up?
Why ask it
Gently invites him to be honest about your house, your town or your street. A polite non-answer means he does not trust the room yet, and that is fair enough.
What's a skill you have that nobody would guess?
Why ask it
A softball, and a chance for him to be interesting on his own terms rather than as somebody's partner. Whatever he names is a safe topic for the next four family dinners.
What was the plan for asking, and which part of it went wrong?
Why ask it
Only ask once the proposal has happened, and let him tell it his way. Every plan has one failure in it, and the failure is the part the family will retell for decades.
Who in your family will we get along with best, and who's going to be trouble?
Why ask it
Playful on the surface, and genuinely useful before a wedding. He will be careful about the second half, so accept whatever he offers and do not push for names.
What's a story about the two of you that your partner tells differently?
Why ask it
Sets up an argument you can watch rather than referee. The disagreement is always about a detail neither of them will let go of.
What are you dreading about the wedding day itself?
Why ask it
Most people ask him what he is excited about, so this is the first chance he has had to say the other thing. Speeches, dancing and small talk are the usual answers, and naming it helps.
What nickname have you been given that you can't shake?
Why ask it
Risky in the best way, because whatever he admits to will be adopted by your family within the hour. He knows that, so the answer he offers is the one he can live with.
What do you want us to stop apologizing for?
Why ask it
An unusual question that almost always lands, because there is something: the noise, the dog, the size of the portions. It gives him a small piece of authority in the room.
What's something you'd like to know about us that you've been too polite to ask?
Why ask it
Turns twenty minutes of questions into a conversation. If he uses it, answer properly, because he has just told you he wants to be part of the family rather than a guest.
What do you think you'll be teased about at family gatherings in ten years?
Why ask it
The best closer here, because it assumes he is staying. Whatever he picks tends to become the running joke, which is not a bad thing to hand him on purpose.
Talking to someone marrying into the family
Practical guidance for the conversation itself
Before you start asking
Remember which way the pressure runs
He is being assessed and he knows it, whatever your tone. That is why the questions here point at his expectations, his own family and his own mistakes rather than at his intentions.
Not in front of the whole table on day one
A round of questions at a full holiday table is a performance, not a conversation. Do this while washing up, in the car, or on a walk with two or three people at most.
Answer them yourself first
Tell your own worst-first-impression story before you ask for his. It costs you nothing and it changes what he is willing to say.
What to leave out
- Money: earnings, debt, who is paying for the wedding, whether he can support anyone. None of it belongs in a light conversation.
- Children and timelines. You do not know what they have already discussed or been through.
- Politics and religion as a joke. It is not a joke to whoever answers wrong.
- Anything comparing him to a previous partner, even favorably.
- Questions with a test buried in them. He will spot it, and the evening will not recover.
What to do with the answers
- Do not repeat a story he told quietly to the whole family later that day. Ask first.
- If he admits to a nickname or a bad habit, teasing him about it once is affectionate and four times is not.
- Follow up weeks later on the specific thing he mentioned. That is what makes him feel remembered rather than interviewed.
- If a question lands badly, let it go entirely rather than explaining what you meant by it.