Somewhere between the sparkling cider and the countdown, New Year's Eve has an hour in it that nobody has planned. That hour is the best one of the night if you fill it with the right questions. A family retrospective closes the year properly: what happened, what everyone learned, what they want next. Below is a full set of questions you can read straight off the page, plus how to run the session so it does not turn into one parent interviewing four bored people.
It works in pyjamas at home, in the car on the way to a relative's house, or on the drive back from a trip squeezed in before school starts. Everyone shares their highs, their lows, the things that surprised them and what they want from the next twelve months.
Why New Year's Eve is the right night for a retrospective
The reflection is already happening. The whole world spends 31 December thinking about what happened and what comes next, so you are working with the current instead of against it. The kids are off school and work has gone quiet, which is the rarest ingredient here: a long conversation nobody has to leave early.
There is also the clock. Looking back deliberately before it resets makes the celebration feel like it was earned rather than just scheduled. And if you do it every year, it becomes the thing your kids expect. That is worth more than any single good answer you get on the night.
How to set the stage
Turn the main lights down and put candles or string lights on instead, with something quiet playing underneath. It sounds fussy. It is the difference between people talking and people waiting for their turn to talk.
Hand out notebooks, sticky notes or put a whiteboard where everyone can reach it, so answers can be written down as they come. Pick a format before you start rather than during: round-robin, small groups, or one person drawing prompts out of a bowl. Say clearly at the top that there are no wrong answers and that honesty is the whole point, because the first person to give a safe answer sets the ceiling for everyone after them.
For the prompts themselves, open MileSmile and run the Family Retrospective game, or build a custom New Year's Eve topic so you never run out mid-session.
Questions to ask
Mix the light ones with the heavier ones. Copy any of these straight into a MileSmile custom deck, or pull them up in Car Mode if you are doing this on the way to a party.
1. Highlights and wins
- What moment from this year would you relive if you could press rewind?
- What personal victory, big or small, made you proud?
- Which family adventure deserves its own photo album?
- Who surprised you in a good way this year?
2. Lessons and growth
- What was the toughest thing you faced this year, and how did you get through it?
- Which mistake taught you something you want to remember next year?
- When did you step outside your comfort zone?
- What did you learn about yourself, or about how this family works?
3. Gratitude and appreciation
- Who showed up for you when you needed support?
- What ordinary moment turned out to be an important one?
- Which family tradition are you most thankful for?
- How did this family make someone else's life better this year?
4. Fun and favourites
- What song, film or book defined this year for you?
- What was the funniest thing that happened in this house?
- Which inside joke deserves a comeback?
- If this year had a name, what would it be?
5. Looking ahead
- What do you want next year's highlight reel to include?
- What is one habit you want to keep, one to start and one to drop?
- Which trip, project or thing you want to learn feels exciting right now?
- How could this family support each other better in the coming months?
6. Rapid-fire lightning round
Finish fast, on answers of one or two words, so the session ends on a laugh instead of trailing off.
- Best meal of the year?
- Most unexpected laugh?
- Favourite new friend?
- Three words for this year?
Running it with MileSmile
MileSmile was built for conversations like this one, and it covers the two places a retrospective usually falls apart.
The first is the car. If you are driving to a countdown event, Car Mode reads each question aloud and takes your answers on the steering wheel controls, so the reflection happens on the way there instead of not at all. The second is running out of material at question nine. Build a Year in Review deck with your family's names, traditions and inside jokes, and the app expands it into as many fresh prompts as the night needs.
Switch modes when the room's energy changes. Family Retrospective for the serious stretch, What Would They Say? and Quick Quiz when the toddlers start losing interest and the teenagers start pretending to. Favourite the answers worth keeping, and next New Year's Eve you can read them back and see what changed.
Traditions worth pairing with the questions
Write the best answers on slips of paper and put them in a jar with the year on it. Opening last year's jar before you start this year's session is the single best upgrade to this whole ritual. Record voice notes too, one per person, each saying their proudest moment out loud, because in ten years the voices matter more than the words.
If the evening is long, ask one question on the hour rather than all of them at once. It keeps the anticipation building towards midnight and stops the retrospective becoming a meeting. And on a long winter drive, let MileSmile run the whole conversation from the first mile to the last.
Including every age
- Give younger kids pictures or emoji to point at, so they can answer how the year felt before they can explain it.
- Put a teenager in charge of the playlist and let them co-host the questions.
- Bring extended family in by video call or a shared MileSmile session.
- React to every answer. Applause, stickers, a confetti popper. Nobody keeps talking into silence.
Pick six questions from this page, write them on a card, and put it next to the cider. That is the whole preparation. Open MileSmile when you are ready for more, and start the year knowing what everyone in the room is hoping for.