I've seen quite a few number of posts over at Board Game Geek over the years about people's negative reaction to board games. It's usually much more prevalent this time of year, as large family gathering are a perfect time to get people together in modest numbers, and usually everyone is looking for something to do. Board games would seem to be the perfect solution. These posts, however, are usually woeful tales of how families simply scatter when anyone even mentions the thought of any type of organized social interaction, let alone a board game.
Personally, I'm not surprised--often, I think people do a poor job of presenting the opportunity to play games, and boardgaming is still a fairly niche hobby. Still, it's particularly frustrating, because we've all seen these games work and everyone have a lot of fun, but getting over the intimidation factor can sometimes be overwhelming.
Here are a few thoughts about the process:
Know your games. Let's get this right off the bat--we're more or less talking about party games when it comes to holiday gatherings. You're not going to get Uncle Charlie who has already downed three shots before breakfast to sit down to a nice game of Wilderness War: The French and Indian War. Of course, you might be able to bring some light card and board games to convince a small group of people to play. But even popular games like Puerto Rico and Agricola aren't going to hit the table--even for fans, it takes too much time and there's usually too much going on for anyone to be able to concentrate. And be aware of the dynamics of the game itself. Large-groups games such as Werewolf are good choices, but even games like Things or trivia games where you can break up into teams to accommodate large groups will work as well. You can get away with some "normal" games like No Thanks or even Citadels if the numbers work out, but it's difficult to find non-party games that are useful with larger groups. Just keep two things in mind: people don't want long, complicated instructions, and people don't want to play a game that's going to last four hours. Pick a game where there is little to no down time, is easy to explain, and that will scale down if necessary. This pretty much rules out all games except party games, and even many of those party games need to be able to be team-based properly to accommodate sizes. What seems to work best are party games that allow teams to freely act--such as shouting out words to guess something, like Password or 25 Words Or Less--than games that allow each player to specifically do one thing and everyone else reacts, such as Say Anything. The latter is often more fun, but the former allows even marginal participants to enjoy themselves. If they don't want to play, they can just sit there, but if they actually want to pipe in, they can.
Know your audience. When you are at family gatherings, you're almost by definition sitting across a large spectrum of demographics--there will be old people and small children and drunk stepfathers and surly teenagers. Trying to coordinate them to do all one thing is going to be a challenge regardless of what you do. Still, knowing how to frame and present playing a game is important. Families and friends may not want to play some weirdo game you have, but if you've played before with an aunt who can vouch for its hilarity, that helps. You may not be able to sell a game to your cousins who aren't allowed to watch television, but you can probably get your XBox-loving nephew to play along. And don't be afraid to adapt. The aforementioned Werewolf is a public-domain game that is perfect for large groups, but not everyone is thrilled about playing a game where a werewolf runs around killing people. Thankfully, it's easy to modify the terms of the game to, say, the mafia, or spies, or pretty much anything else.
Know the numbers. What games you select and how you present it is going to be vastly different whether there will be eight people there or twenty. There are very few games that work with more than eight players, unless it's a team-based game. And it's not a sin to exclude people--if you know that only ten people out of fifteen want to even try and play, then just include those ten. If the others get jealous, well, there's always time for another game.
It is not the time for conversion. There is a time and a place to convert people into playing modern board games, but this isn't it. It's tempting, since you have a large audience of people looking for a social pasttime, but it's almost always the wrong place and the wrong time.
Know when to sit down. The harsh reality is that not everyone wants to play games. While for many families the holidays are a time to gather together and have fun, you are also bringing different personalities into one room. And people may be more interested in visiting with others they haven't seen all year than playing your silly variation of Taboo. Time is short, things need to get done, and often even if you pull off getting everyone to play along, the slightest moment of boredom will get them to lose interest. Sometimes, it's better to bring a standard game, like Ticket to Ride or Pandemic and play with just a small group of people that you know will have fun, and if onlookers are interested they can join in a larger game later. (Resist the temptation to bring games like Small World or Dominion; while they are fun for medium-sized groups, their themes and artwork are hardly a good choice to convince non-gamers to play.) Just don't be too disappointed if you're confined to the couch watching ice skating and eating sugar cookies all afternoon.