Start by setting the mood with some music, drinks, and other familiar diversions.
If you want everyone to be in the mood to chill for, like, a second and enjoy themselves, cue them in to the kind of gathering you want to have from the get-go. It doesn't have to be anything groundbreaking, but enough to start everything off on the right foot. Some ideas:
• Pull out old family photo albums and leave them sitting out on coffee table or side table. People will naturally pick them up and start flipping through them, and sharing stories/memories.
• Aaand if none of that is your style, you could share stories from some truly WTF articles, like this one about poop knives, this one about the worst guy ever, this one about another fuckin' guy, this compilation of truly wild work advice columns, or a compilation of terrible relationship advice questions. All bound to spark friendly conversation and debate!
And work in an icebreaker or several.
A few "Name one interesting fact about yourself" prompts too many have sullied the good name of icebreakers, but it's not too late to rehab their reputation. It doesn't help that the word "icebreaker" itself is a misnomer. Like, surely the ice has been broken (albeit perhaps re-frozen) among family? Regardless, if you think of these questions instead as room-warmers, maybe you'll feel more positively toward them. If not, surely these specific room-warmers will appeal to you:
• If you could, would you have a personal trainer, personal chef, housekeeper, or personal glam squad?
• If you could pick up a new skill in an instant, what would it be?
• What's your favorite word?
• What song would you pick to play as you walked up to bat at a professional baseball game?
• We all know about red flags, but what do you consider to be a "green" flag when you meet a new person?
• Ignoring your actual age, is there an age you feel like you're stuck at?
• What's your favorite condiment?
• How do you like your eggs?
• Would you rather only be able to use toilet paper as paper towels, or vice versa?
• What's one place you've never been that you'd like to travel to, and one you've been to and want to go back to?
Basically, make it light, unexpected, and narrow enough that it won't take forever for people to think of an answer. And if none of those work for you, one of these or these will surely do. You can try these out in one-on-one conversations, or kick off the whole event with one. It's really your call.
And if you're feeling awkward about launching one out of the blue with a family that doesn't really do things like this regularly, you can always lead with something like, "Some of my friends/coworkers and I were discussing this question the other day and I'm still thinking about it" to make it feel a little more natural.
When it comes time for dinner, guide the conversation with a topic that's deep, weird, thought-provoking, or maybe all three.
Room-warmers are great and all, but they aren't designed to sustain an engaging conversation for more than a few minutes. Beyond that, they generally don't get too deep — and really, we often don't know our family or friends as well as we think we do (or want to). These topics might help, though:
• Ask everyone to share what they're proud of, but never have an excuse to talk about. Sure, this sets things up to be a bragging contest, but it also sets up a way for people to share what really matters to them. Sometimes, it can be hard to understand people's motivations, which can lead to conflict and frustration, but this can be a way to hear what they consider to be a foundational part of what makes them them. And if they say something cool, then you’ll get to brag/talk about their story in the future.
• If that seems like a guaranteed way to to turn everyone into intolerable braggarts, go around and say your favorite thing about each person in the room. My friends and I did this at a gathering a few years ago, and it was so earnest and heartwarming. I found out that I spend shockingly little time thinking about the specific things that make me like each of them individually, and this was a delightful way to spread warm-fuzzies and feel gratitude for loved ones.
• 15 Toasts: As Priya Parker explains in her book The Art of Gathering , this is when everyone in a group of people (it can be more or less than 15, FYI) shares a toast to a particular theme. The theme can be the good life, friendship, values, trust, the list goes on. Each person's toast can be as short or long as they'd like, but the kicker is that the last person to give a toast has to sing theirs. You'll be surprised at the depth and variety you'll get from each person's story, and thanks to the singing aspect, people will be eager to share.
And when there's some downtime, opt for a game or activity that actually everyone will enjoy, I promise.
There's bound to be people of all ages and abilities, but keeping some go-to diversions in your back pocket will come in handy when you're bored, overstimulated, annoyed, or if you're really lucky, all three! Some favorites:
• Celebrity: This is a fantastic group game, and all you need for it is some pens, paper, and a bowl/hat/vessel that can hold a bunch of slips of paper. Each person writes down 3-5 names on pieces of paper, and the names can be anyone — family members, celebrities, fictional characters, historical figures, just anyone that everyone in the group will know. All of the papers go into the bowl, the group divides into two teams, and then everyone takes turns describing the name on each piece of paper to their team until the bowl is empty. Then, they all go back in the bowl, and in round two, everyone describes the names on the papers using just two words. In round three, people act out the names using charades.
• Codenames: I've spent a majority of 2018 bullying everyone I know into learning how to play this game, and not one person hasn't loved it. It's a word association game that's ideal for 4-10 people, it's relatively easy to learn how to play, and it gets even better when you're really on the same wavelength as someone else on your team. I can't do the rules justice, so read them here.
• Create a quiz to see who knows a beloved family member best. Cup of Jo recently shared a template of this sweet way to honor and celebrate someone in your family (and complete for prizes based on who knows the most).
• Any of these fun, silly family party games.
• A puzzle...but if there are little kids with grabby fingers loitering around, maybe think twice about this option (or put it on a really high table).
• Or you can have everyone figure out their astrological birth chart. You can gamify this (and the above) by having everyone write down their results, scramble them up, and then guess who's who based on the descriptions.