Start with the guest list
Before picking games, count who is actually coming. Player count shapes the evening more than anything else, because every game has firm limits. Village at Night needs at least five people, Say It Different and Cover Word need four, while Sketch Round, Quiz Night, Letter Hunt and Fib Finder top out at ten.
With three to six people almost everything works, including Corner Chaos and the card games. Once you hit seven or more, the night naturally turns into a party: Crazy Mau goes up to eight, Thirty-One up to nine, the team games up to twelve. Have one or two more games in mind than you need and read the room instead of working through a fixed list.
Think in an arc, not a list
A good game night has a shape. Early on, people are still arriving and chatting, and nobody wants a long rules explanation. In the middle, the energy peaks and loud team games and bluffing fit perfectly. Towards the end things calm down, some people need to leave, and a quick card game beats starting something long.
That gives you three phases: a warm-up with games you can explain in one sentence, a party phase with the games people talk about for days, and a wind-down where someone can drop out without the game falling apart.
Warm-up: easy to explain, instantly playable
Quiz Night is a great opener because everyone gets it right away: the question is on the TV, four big answer buttons are on your phone, and you have 20 seconds. Before you start you choose the categories and the number of questions, so you decide how long the round lasts.
Letter Hunt works the same way: a letter on the TV, categories on your phone, and time is up after three minutes at most. If there are six of you or fewer, Corner Chaos gets everyone laughing. Your phone becomes the steering wheel, and computer drivers fill any empty spots.
Party phase: teams, drawing, bluffing
Now everyone is warmed up and it can get loud. Say It Different splits the group into two teams, and one person at a time explains words for 60 seconds without using the forbidden ones. Cover Word is quieter and trickier: each team's clue giver hunts for a single word that links several words on the board.
Sketch Round and Fib Finder produce the funniest moments. In Sketch Round the drawing appears live on the TV, and in Fib Finder everyone invents a believable fake answer and hopes the others fall for it. With five or more, Village at Night is the highlight of many evenings. The TV narrates so nobody has to run the game, but leave plenty of time for the arguments.
Wind-down: cards and dice
Close with games that play in short rounds. Little Max is ideal if there is still some energy left: everyone has three lives, you roll secretly on your own phone, and bluffing is the whole point. Thirty-One and Crazy Mau are familiar card games, and with phones nobody has to shuffle.
If only two or three of you are left at the end, Five Dice is a good pick. It runs without a TV, and if you are missing a player, the computer can step in.
Check the tech before people arrive
Open Gather once on your Apple TV, iPad or Mac before guests arrive and join with one phone. It's easiest if all devices are on the same Wi-Fi. Guests without the app just scan the QR code on the TV and play in their browser. Put the Wi-Fi password somewhere everyone can see it; that saves more time than anything else.
Don't switch to another app on Apple TV during a game, or the phones lose their connection until Gather is back in front. The rules for every game are right in the app if questions come up.