How to choose games for multi-generational family gatherings
Getting a nine year old and a ninety year old to enjoy the same thing is a real problem, and the usual answer of picking something for the middle satisfies nobody.
The actual difficulty
A family gathering can span seventy years of age, three levels of eyesight, wildly different reference points, and at least one person who is only there under duress.
The instinct is to find something in the middle. This is usually a mistake, because the middle is where things are mildly acceptable to everyone and genuinely fun for nobody. What you want is a game that gives different people different ways to be good at it.
Reward more than one kind of clever
A game that only tests general knowledge belongs to whoever reads the most. A game that only tests reflexes belongs to the teenagers. Either way you have handed the evening to one demographic, and everyone else is playing a supporting role in someone else's win.
The games that work across generations reward several things at once: a sharp eye, a good memory, a bit of nerve, and enough luck that nobody is ever completely out of it. When a grandchild can out spot a parent and a grandparent can out guess a teenager, the whole table stays interested.
Simple enough to start cold
The explanation is where you lose people. Anything requiring a five minute briefing has already lost the youngest child and quietly humiliated the relative who did not follow it and will not ask.
A game you can start playing before you have entirely finished explaining is worth ten clever ones. Simplicity is not a compromise here. It is the whole qualification.
Watch out for the technology gap
Not everyone is comfortable with anything that needs setting up. If joining in involves an account, an install, or a settings menu, some relatives will decide in advance that this is not for them, and they will be polite about it and mean it absolutely.
Whatever you choose, the barrier to joining should be close to zero. The moment it feels like a technical task, half the room opts out.
Let the oldest and youngest team up
Pair them deliberately. The child gets an ally and someone to show off to. The grandparent gets an actual role rather than a chair at the edge of things.
It also solves the confidence problem. A nine year old who would never shout an answer alone will happily shout one with a grandparent nodding along beside them.
Make it the thing you always do
The gatherings people remember fondly tend to have something that always happens. Not a schedule. A habit.
If it is easy enough to repeat without anyone having to organise it, a game stops being an activity somebody suggested and becomes part of what the family is. That is worth more than picking the perfect game, and it is a much lower bar than most people assume.