15 conversation prompts to connect on a deeper level without making it weird
These "reflective" topics are meaningful but not overly personal.
When family and friends gather together, conversations can go a few ways. If you’re genuinely close and used to sharing openly, conversation may flow naturally with no need for assistance. If you’re getting together with people you rarely see, don’t know very well, or struggle to connect with, however, conversations can feel mundane, stilted or awkward. Even with family, a 50-year-old trying to talk to a 15-year-old extended relative can be difficult without knowing what questions to ask.
Whether we’re getting together with people we know or people we are meeting for the first time, it’s nice to be able to go a little deeper than talking about the weather or pop culture. Politics is a minefield, now more than ever, and not everyone wants to share the nitty gritty details of their personal lives, so it can be hard to figure out how to have meaningful conversations without making it weird.
Ordinary & Happy offers a list of “reflective topics” that can help improve conversations with anyone of any age. Here are some examples of questions based on their suggestions and some reasons they're so effective.
Looking back
What’s something you learned this past year?
Who was an influential person in your life last year?
What’s something you accomplished this year that surprised you?
The good thing about looking back over the past year is that the experiences are fairly fresh. A year is a good amount of time to think about because it’s short enough to not be overwhelming but long enough to have had some interesting experiences and learnings.
Looking again
What’s something you rediscovered a love for?
What’s something or someone you’ve reconnected after a long time?
What’s a place you’ve visited that you really enjoyed?
A twist on reflection, adding a “re” element by asking someone about something they might have forgotten about or disconnected from but found again can be a fun way to think about the previous year a little bit differently. And of course, places we’ve enjoyed visiting is always a solid topic.
Looking ahead
What’s something you want to improve on next year?
What’s a goal you have for next year?
What’s something you’re looking forward to next year?
It can be a little tricky to ask people about the future, especially young people who often feel a lot of pressure to have their futures figured out. But on a personal level, we all have things we’re looking forward to as well as intentions for our future, even if we don’t know how it’s all going to play out.
Looking inside
How has your perception of time changed?
Have your values shifted or changed and what prompted it?
What’s something you learned about yourself this year?
These questions offer a way to get to know someone without asking about too-personal topics. Values might be considered personal, but there are a lot of ways to ask people about how the way they see the world or themselves has changed.
These prompts can work in a group or one-on-one conversations.Photo credit: Canva
Looking at being human
What do you believe is a key to good communication?
What do you believe is one of the best ways to build trust?
What do you believe the last year taught you about life?
Broadening the questions to more general human experiences rather than focusing them on an individual is a good way to pivot if people seem to feel uncomfortable talking about themselves. The adage “People love to talk about themselves” isn’t always true, but most people will weigh in on a light philosophical question like “What do you think makes someone a good friend?” or “What do you think the world needs more of?”
Anyone can come up with these kinds of reflective questions. A few tips to keep in mind, though:
- Try to avoid words like “favorite” or “best” unless you preface it with “one of.” You don’t want to force people to sort through their thoughts and put them in a particular order. Some people may have one favorite place or memory, but more often than not there are many things that could compete for that title and trying to narrow down one makes people freeze up.
- Stick to universal human experiences. We’ve all discovering things about ourselves and the world all the time, but we’re not all into the same things. “What’s a place that makes you feel peaceful?” works better than “What’s your favorite place to vacation?” Keep questions broad and focused on human characteristics instead of niche experiences people may or may not have had.
- Put questions into your own words. You might not say, "What's one thing you learned this year?" For you, it might be, "Hey, tell me about an interesting learning experience you had this year. What stands out to you?" The more natural the question in your own voice, the better. It's the topic that matters, not the wording.
Happy conversating!