Last Tuesday at 4:15 PM, I sat in front of my monitor and watched a grown man in a $200 ergonomic chair try to explain the rules of a digital scavenger hunt to fourteen people who clearly wanted to be doing literally anything else. I had a lukewarm seltzer in my hand and a mounting sense of dread in my chest. We were ‘bonding.’ Or at least, that’s what the calendar invite—the one that had been haunting me since Monday morning—claimed we were doing.
It was miserable. It wasn’t just boring; it was actively draining. I felt more disconnected from my coworkers after that hour than I did when I woke up that morning. And that is the problem nobody wants to admit: your virtual happy hours are making your team hate their jobs more, not less.
The Tuesday afternoon I almost quit because of a trivia bot
Let me tell you about the breaking point. It was October 2022. I was working for a mid-sized tech firm—good benefits, decent people, the usual. Our ‘Culture Committee’ decided that because engagement scores were dipping, we needed a ‘Digital Mixology Night.’ They sent us these kits with tiny bottles of bitters and plastic shakers. On the surface, it sounds nice, right? Free stuff. A break from the grind.
But here is the reality: I had three deadlines looming. My kid was screaming in the next room because he couldn’t find a specific Lego piece. And there I was, forced to keep my camera on, trying to look ‘enthusiastic’ while a professional mixologist named Derek told us about the history of the Old Fashioned. I didn’t want a cocktail. I wanted to finish my work so I could stop looking at a screen. I felt like a hostage in my own home office. I actually looked at my bank account during the call to see if I could afford to quit right then and there. I’m not even kidding. The sheer performative nature of it felt like an insult to my intelligence.
Mandatory fun is like a room-temperature glass of milk—nobody asked for it, and it leaves a bad taste in your mouth.
I tracked my ‘eye-roll count’ during these mandatory social sessions for about six months. In my last role, I averaged 12.4 eye-rolls per 30-minute session. That’s a scientific fact. Okay, maybe I just tallied them in a notebook, but the data is real to me. When you force people to socialize, you aren’t building a culture. You’re building a resentment factory.
Connection isn’t a scheduled event
People think ‘culture’ is something you can manufacture with an app or a Slack integration. It’s not. I used to think I was wrong about this—I used to think maybe I was just an introvert who didn’t ‘get it.’ I was completely wrong. Even the extroverts on my team were private-messaging me during these calls asking when they could leave.
What I mean is—actually, let me put it differently. Real connection happens in the gaps. It happens when you’re both struggling with a weird bug in a spreadsheet and you hop on a quick call and end up talking about your favorite bad movies for ten minutes. It’s organic. You cannot force fourteen people into a Zoom square and tell them to ‘be friends’ for an hour. It’s awkward. It’s performative. It’s exhausting.
Connection is a byproduct of shared meaningful work, not a replacement for it.
Why I’m officially done with Slack ‘Donut’ calls
I know people will disagree with me here, and honestly, I don’t care. I hate Donut. For those who don’t know, it’s a Slack bot that pairs you with a random coworker for a ‘coffee chat.’ It sounds lovely in a HR handbook. In practice, it’s a 20-minute exercise in trying to find common ground with a stranger while you both secretly check your email.
I once got paired with a guy from the legal department. We spent fifteen minutes talking about the weather in Ohio. I live in Oregon. He didn’t care about my rain; I didn’t care about his humidity. We both knew it. We were just two people performing ‘engagement’ for the sake of a metric. It felt hollow.
I refuse to use these tools anymore. I’ve muted the notifications. I know it makes me look like ‘not a team player,’ but I’d rather spend those twenty minutes actually doing my job so I can log off and talk to my real friends. Is that unfair? Maybe. But I think we need to stop pretending that every coworker needs to be a best friend.
Work is work.
The part nobody talks about: Your process is the problem
If your team is disengaged, it’s probably because your meetings are too long, your expectations are blurry, or your boss is a jerk. It is almost never because you haven’t played enough Jackbox games together. I’ve noticed that the companies that push ‘virtual fun’ the hardest are usually the ones with the most toxic work-life balance. It’s a distraction tactic. It’s ‘People Ops’ corporate babysitting for adults who are burnt out.
I might be wrong about this, but I think middle managers who love these events are usually just lonely. They miss the office because their identity is tied to ‘managing,’ and they can’t manage if they can’t see people’s faces. So they force these social hours to feel a sense of control. It’s selfish. There, I said it.
Here is a short list of things that actually make me feel ‘engaged’ at work:
- Getting clear feedback that isn’t wrapped in a ‘compliment sandwich.’
- Having a manager who trusts me to pick up my dry cleaning at 2 PM without asking for permission.
- A Slack channel where we can actually complain about stuff without feeling like HR is watching.
- Being paid what I’m worth.
- Meetings that end 10 minutes early.
That’s it. That’s the whole list.
What actually worked (and it wasn’t free)
I remember one time—this was back in 2019, just before everything went sideways—my team was really struggling. We were all remote, all stressed. Our lead didn’t schedule a happy hour. Instead, he gave us all a Friday afternoon off and $50 to spend on ‘something that makes you happy.’ The only rule was we had to post a picture of what we did or bought on Monday.
People bought books, fancy coffee beans, or took their kids to the zoo. On Monday, we actually talked about those things because we were refreshed, not because we were forced to drink on camera. We spent maybe $600 total as a team. The ROI on that was massive compared to any trivia night I’ve ever attended.
Anyway, I’m rambling. The point is that remote work is a different beast. You can’t just take office culture, put a digital filter on it, and expect it to work. It’s like trying to use a fork to eat soup. It’s the wrong tool for the job.
I despise Mural, by the way. I know everyone loves it for ‘brainstorming,’ but it’s a digital whiteboard that feels like trying to paint a house through a keyhole. It’s over-engineered and unnecessary. Just give me a bulleted list in a shared doc. Stop making things ‘visual’ just for the sake of it.
A recommendation with zero fluff
If you are a manager and you’re reading this: cancel your next virtual happy hour. Just do it. Send an email right now. Tell them you’re giving them that hour back to do whatever they want. I guarantee you’ll see a bigger spike in morale than any ‘Guess the Workspace’ game could ever provide.
I don’t have all the answers. I don’t know how to perfectly solve the loneliness of the remote worker. Sometimes I get lonely too. But I do know that the solution isn’t more ‘forced fun.’ It’s respect. It’s boundaries. It’s acknowledging that we are all adults with lives outside of this glowing rectangle.
Will people be mad if you cancel the trivia? Maybe one or two. But the rest of them? They’ll be too busy enjoying their silence to complain.
Worth every penny.