Dear OOO,

A couple of coworkers have been planning virtual events for our office—happy hours, trivia sessions, and the like. These happen at the end of the day when I’m exhausted, trying to finish my work so I can log off, and sick of Zoom. So I haven’t been going. But in an effort to “get more people involved,” a couple of other abstainers and I got tapped to plan the next event. So … what makes a good virtual office hangout, and how do I turn this into something I won’t hate?

—Sara, Chicago

The short answer, Sara, is that you should play Jeopardy. Everyone loves Jeopardy, and Jeopardy Labs allows you to create boards with any categories you want, whether obscure art history or obscure office in-jokes. (I swear this is not sponcon for this random website.) The closest thing to fun I have experienced during many, many quarantine virtual hangouts were the ones involving Jeopardy.

That said, we are missing one crucial piece of information: How big is your office? Jeopardy isn’t going to work with more than five or six people, and it’s no fun to watch other people play trivia. The vast majority of activities that can be played online, in fact, are going to be much, much less fun with more than a handful of people. Games are out if you don’t have a tiny workplace. (Assuming you don’t work for a tiny company, can you plan something for your department instead of the entire office?) There are the experiential options—cooking class, magic show, you get it—but here we run into a related problem. Only the most outgoing of your colleagues are going to talk and the rest of you will be watching a performer banter with a couple of class clowns. Silently. Sounds thrilling!

That leaves the generic “happy hour” approach. This, in my humble opinion, is the worst-case scenario. (Apologies to everyone who has invited me to a virtual happy hour over the past 14 months; you’re all perfect angels and I’m certain your happy hours are great.) Video chat is slightly stilted at baseline; social cues are harder to read, conversational timing is harder to synchronize thanks to various internet delays. The more people you add to the room, the worse those problems get. Above six people or so, everyone is bound to talk over each other—or worse, they remain silent because they’re terrified of talking over each other. I’ve seen people try to add a discussion prompt to guide the conversation and give everyone a chance to talk, but then you risk things feeling too much like any other meeting, or kindergarten show-and-tell.

Of course, even purely social hangouts in the age of coronavirus run into these problems. Layer on office politics, then, and you’re bound for trouble (and we haven’t even grappled with the thorny question of whether to drink on screen but alone in your living room). A paper out this week from the Journal of Applied Psychology found that the more disconnected people felt to others on a videoconference, the more fatigue they felt afterward. Ergo, a hangout with colleagues you don’t know well is likely to leave you more exhausted, less pleasantly party-buzzed. The beauty of an IRL office gathering is you can bounce from group to group; online, you’re captive to that guy who kidnaps every conversation. In most of these virtual events, there’s just not enough of a shared sense of purpose to make things flow naturally. If you and your coworkers all work in the same place, I can offer an unqualified endorsement for park gatherings, which have become a staple for WIRED’s teams in San Francisco and New York.

If you’re dispersed, though, Jeopardy remains my answer. For other options, my less curmudgeonly colleagues have published all sorts of excellent guides to online karaoke and party games and movie watch parties and remote co-op gaming. All of them have failed to convince me that I want to spend more time online with a group of my (wonderful!) colleagues after hours, but your mileage may vary.