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Having a get together with your girlfriends? Planning a moms’ night out? I love these kinds of events — the best ones foster a sense of camaraderie and joy that is refreshing and life-giving. Alas, the worst ones can become a hotbed of gossip and complaining that leave no one refreshed. In between those two extremes are a lot of mediocre evenings where the conversation gets stuck in a superficial loop.
I often look for a way to break out of that and bring the conversation deeper. One way to do that is to find conversation starters. I often google something like “best questions for girls’ night,” and while I find many decent questions out there, they are often mixed with less effective questions or just awkward non-starters.
Here are a couple of strategies for making questions feel more natural and less formal, as well as some specific questions I’ve found that work well.
1
FUN STARTERS
Always start with fun questions before moving on to deeper ones. If you want people to feel comfortable sharing about deeper things, they have to build some rapport and be willing to share in the first place. That may only take a few fun questions if you have a group of friends who know each other well.
If you have a larger group, then it will take a while for everyone to share something – but that will let people naturally hop in and keep the momentum going. On the other hand, if you have a smaller, less-connected group, it will probably take people a little longer to feel comfortable.
Some examples of fun questions that don’t require much vulnerability:
- What’s your all-time favorite vacation destination?
- Can you name your favorite thing to splurge on?
- Who was your celebrity crush growing up?
- Do you have a favorite family memory from growing up?
- What’s a time period that you wished you could have lived in, and why?
2
DEEPEN THE CONVERSATION
After people have started getting into a groove with sharing, here are a few questions that may help move the conversation a bit deeper:
- What’s the most thoughtful gift you have ever received?
- Do you have a book that has influenced your life and can you explain why?
- Is there a part of your day you like best?
- What is your favorite day of the week and why do you like it so much?
- Where do you feel most “at home” in the world?
3
TAKE IT TO THE NEXT LEVEL
Once everyone has hopefully shared some things (or it seems like a good time to move on), here are some good questions that may lead you even deeper:
- Can you describe a time when you felt immense joy and wonder?
- When have you felt the most proud of yourself?
- How do you hope to change and grow in the next five years?
- What activities or moments have made you feel most fulfilled in life?
- Can you identify a difficult time or challenge in your life that has made you stronger, and how?
If you are the official facilitator (or unofficially make this your job), try to make sure everyone has had a chance to answer each question. No one should feel obligated to answer, but some personalities don’t know how to jump in and may need a nudge from someone else to help them find an opening.
Hopefully these questions can spark other good ones and keep your conversations lively and meaningful.
And today we celebrate...