When's the last time a conversation actually surprised you?
Not small talk about the weather. Not a recap of what everyone watched on Netflix. A real conversation — one that made you think, laugh, or see someone in a completely new light. If you're struggling to remember, you might be overdue for an upgrade. Here are five signs your conversations could use a serious boost.
1. You already know how every conversation is going to go
You see the same people, you talk about the same things, and nothing anyone says catches you off guard. Predictability is comfortable — but it's also a sign that you've stopped really connecting. Great conversations have an element of surprise. If yours don't, it's time to shake things up.
2. Your phone is always within reach — just in case
When a conversation gets quiet, the instinct is to reach for your phone. But that silence? It's actually an opportunity. The best conversations happen when there's nowhere to hide and everyone's actually present. If your phone is your escape hatch, you're missing out.
3. You leave gatherings feeling kind of... meh
You showed up, you chatted, you went home. But you don't feel energized or connected — just like you checked a box. That post-hangout flatness is a sign that the conversations didn't go deep enough to matter. Good conversation leaves you feeling more alive, not less.
4. You don't know what your friends actually think about things
You know their job, their relationship status, their weekend plans. But do you know their unpopular opinions? Their weirdest beliefs? What they'd do if they won the lottery tomorrow? If the answer is no, you're stuck at the surface — and there's so much more underneath.
5. You dread the "so, what's new?" question
Because nothing feels new. Or because you don't know how to answer it in a way that leads anywhere interesting. That dread is a signal: the conversation format you're using isn't working. You need better questions — ones that actually open people up.
The fix is simpler than you think
Better conversations don't require a therapist or a life coach. They just require better prompts. Questionably Decided is a party game built around questions that get people talking — really talking. The kind of conversations you'll still be thinking about the next day. Try it at your next gathering and see what happens when everyone actually shows up to the conversation.