Questions to Ask Favorites
Favorites questions built to get past the one word answer: what someone rewatches, what they own that cost nothing, what they do with an empty day. Written for a first date, a long drive, or a dinner where you want light conversation that still tells you something.
The questions
Open any question for the note
What's your favorite meal that someone else makes?
Why ask it
Naming a cook as well as a dish hands you a person and a kitchen in one answer, which is far easier to talk about than a cuisine. Most people go to a parent or a grandparent here, and the food turns out not to be the interesting part.
What's your favorite way to spend a day with nothing in it?
Why ask it
An empty day is more revealing than a weekend, because there is no plan to hide behind. Notice whether the answer involves other people or none, and whether it costs anything. That is a fair preview of what living alongside them looks like.
What's your favorite album, rather than your favorite song?
Why ask it
Songs come off playlists; an album means they sat with something. Asking for the record usually gets a period of their life attached, because people pick what they listened to during a particular year rather than the best thing they know.
What's your favorite thing you own that cost almost nothing?
Why ask it
This sidesteps the status answer that questions about possessions normally produce. A ticket stub, a chipped mug, a tool that belonged to someone: whatever they pick, the reason is a story, and the reason is the entire point of asking.
What's your favorite place you have been on your own?
Why ask it
Taking the company out of the trip leaves only what they actually liked about it. It also shows how comfortable they are alone, which is more informative than asking whether they consider themselves introverted.
What's your favorite time of day, and what are you usually doing then?
Why ask it
The second clause turns a preference into a description of their real routine: early and quiet, awake after everyone else has gone to bed, the hour after work before anything is decided. It is the shortest route to how their day is actually shaped.
What's your favorite film you have seen more than three times?
Why ask it
Rewatching is a better test than ranking, and it rules out the respectable answer people give to look serious. What someone returns to is usually about comfort or a specific year, and they will often admit that unprompted.
What's your favorite thing to spend money on that other people would call a waste?
Why ask it
This gets at values without asking about values. Books, good coffee, taxis home, a hobby with expensive consumables: the answer shows what they refuse to economize on, which matters more than it sounds in any shared life.
What's your favorite thing about where you grew up, and about where you live now?
Why ask it
Asking both invites a comparison they may never have made out loud. Whether the second answer is warmer than the first tells you how settled they feel, and whether the move was chosen or just happened to them.
What's your favorite book you would never recommend to anyone?
Why ask it
The qualifier is what makes it work. It gives permission to name something unfashionable or embarrassing, which is more fun and considerably more honest than a favorites list assembled to be defended.
What's your favorite thing you have learned to do as an adult?
Why ask it
Adult learning is chosen, unlike school, so the answer shows what they were willing to be visibly bad at. It also surfaces skills, swimming, driving, cooking, a language, that otherwise never come up in ordinary conversation.
What's your favorite thing about your job that would never appear in a job description?
Why ask it
It sidesteps the small talk version of the work question. Answers tend to be a colleague, a quiet hour, a machine, a drive, and they tell you much more about how the week actually goes than a job title does.
What's your favorite compliment you have ever been given?
Why ask it
People remember one, often word for word, and the fact that it stuck says something about what they doubt in themselves. Notice whether it was about their character, their work, or how they look.
What's your favorite meal you can cook without looking anything up?
Why ask it
Easy to answer and it establishes what actually gets made on a Tuesday rather than what they aspire to cook. If nothing comes to mind, that is useful too, and it is usually said with a laugh rather than embarrassment.
What's your favorite thing to do with other people, and your favorite thing to do without them?
Why ask it
Putting both halves in one question stops the answer from being purely sociable. The split between the two is roughly where their appetite for company runs out, which is worth knowing before planning a weekend together.
What's your favorite piece of advice you actually took?
Why ask it
The word actually rules out the sayings people repeat without following. A real answer names who said it and what they did differently afterwards, which is a better window than any question about their outlook on life.
What's your favorite thing to argue about?
Why ask it
Almost everyone has a subject they enjoy disagreeing over, and hearing it early shows how they argue: for sport, to win, or to think. It also marks out which topics are not in that category, which is the more useful half.
What's your favorite tradition, and did you inherit it or start it?
Why ask it
The second half is where this gets interesting. Inherited traditions tell you about their family; invented ones tell you what they felt was missing and decided to build, which often follows a move or a loss.
What's your favorite version of yourself, and when were you like that?
Why ask it
Heavier than the rest, so leave it late. An answer set in the past usually arrives with an account of what changed, and someone who names the present is telling you something worth noticing as well.
What's your favorite thing about someone you love that they don't know you notice?
Why ask it
A warm place to finish, and it shows how they pay attention, which is more telling than asking how they show affection. The good answers are small and specific: a habit, a phrase, the way someone stands in a queue.
Using favorites questions well
Practical guidance for the conversation itself
How to ask them
Always take the follow-up
The favorite itself is trivia. The reason behind it is the conversation. When someone names a film, a dish or a place, the next thing out of your mouth should be when, or who with, or what was going on that year.
Answer your own question too
These work as an exchange and fail as a survey. Give your answer either first or immediately after, with the same amount of detail you are hoping for, and the other person will match your level rather than yours matching theirs.
Ask for a specific one, not a category
Favorite music produces a genre; favorite album produces a story. The narrower the question, the better the answer, which is why the useful versions of these questions have a constraint built in.
Follow the energy rather than the list
If one answer opens something up, stay there for ten minutes. A list is for when the conversation stalls, not for working through in order, and abandoning it is usually the sign it is going well.
Where these work and where they do not
- Good on a first date, where a light question with a real answer beats an interview about work and family.
- Good in a car or on a walk, where side by side makes a slow answer comfortable.
- Good with someone you have known for years, since the specific versions rarely come up by accident.
- Weak in a group larger than four, where each person gives a headline and nobody expands.
- Weak over text, where the reason gets dropped and you are left with a list.
- Weak as an icebreaker at work, where anything about love, money or self-image will not be answered honestly.
Common pitfalls
Rapid fire
Six of these in a row turns into a quiz, and the answers get shorter with each one. Two or three in an evening, spaced out and followed up, is the whole set anyone needs.
Grading the answer
Reacting to a favorite with surprise, teasing or a correction ends the honest version immediately. What comes next will be chosen for how it sounds rather than for being true, and you will have taught them to do that all evening.
Waiting to talk
Asking a question while holding your own answer ready is visible from across a table. Listen to the reason they give and ask about that instead of arriving with your prepared story.
Mistaking taste for character
What someone likes is far less informative than why, and drawing conclusions from a band or a book usually says more about you. Treat the favorite as the door rather than the room.