As my kids have gotten older, I’ve noticed my circle of friends has gotten smaller.
It’s not that I’m antisocial now. It’s just that having kids tends to create quick and plentiful connections.
You’re thrown in the path of other adults through your children’s’ school, sports activities, and social events and can make some easy friendships. Once my kids could drive, I didn’t need to attend most of their activities. And once they moved out of the house, these child-related social events dried up completely.
Also, since I work from home, I’m not in an office environment that has other people with whom I could establish friendships. I figured out pretty quickly, if I wanted to broaden my circle, I needed to get out there and make new friends. It’s not as easy as it was in second grade when you just found a kid who looked approachable and said, “Hey you wanna be friends?”
Adults are busy and preoccupied, and most of us are past the time of wanting to foster casual friendships. One of the best ways to determine if someone has friend potential is by having a conversation with them. Not just a casual conversation — but a more intimate, open conversation in which you both reveal elements of your true selves.
This can take some finessing when you first meet someone. You don’t want to scare them away with a probing question like, “So how’s your sex life?” Nor do you want to waste time with too many “What do you think of this weather?” type of questions. Some of the best questions to create closeness and interest are open-ended questions that require more than a “yes” or “no” answer — and that invite deeper conversation between the two of you.
Here are 15 good conversation starters to foster connection and eventual friendship:
1. Tell me about your upbringing.
You can learn so much about someone when they talk about their childhood and family of origin. This gives you the opportunity to find common ground and similar life experiences. You will likely have the same question sent back to you, so it allows you to openly share parts of your personal life experiences as well.
2. What first attracted you to your spouse/partner?
It’s always fascinating to hear how someone met their love partner. The qualities they found attractive in another person gives you insight into their values and their own personality traits.
3. Tell me about your most memorable, meaningful travel experience.
Travel is always enlightening and expansive. Sometimes a trip is life-changing — it’s more of a journey than a vacation. People always enjoy talking about these experiences and how passionate and alive they felt during them.
4. What are you most proud of?
This is a great question because it invites the other person to freely talk about their accomplishments. We all want to feel valued and useful, and knowing someone is interested in our successes breaks down emotional barriers and discomfort.
5. What is the best life lesson you’ve every learned?
This question often evokes some true “ah ha” moments, as most people don’t take time to think about life lessons. Experience is a great teacher, and over time we all learn from our successes, mistakes, past encounters, and years of experience. Being able to talk about your own life lessons is a sign of emotional maturity and self-esteem.
6. Tell me what’s on your bucket list.
When someone has a bucket list or a list of goals before they die, it shows they are engaged in life and want to experience it to the fullest. The follow-up question to this one is, “What plans are you making to check off the items on your list?” You may find you share many similar items on your list. In fact, you might be creating a new friend with whom you share these bucket list items.
7. You look (happy, sad, bored, uncomfortable). Am I right, and what’s going on?
When you ask someone this question (in a kind, non-challenging way), it shows you can read people or at least want to attempt to understand what’s behind the facade. Sometimes a person can be flooded with emotion, and they just need someone to cue them to open up. Offering a warm and caring space for someone to share how they’re feeling is a great way to start a friendship.
8. What books have you read recently that you really loved?
What we read tells the story of who we are and what intrigues us. When you find you share a common reading list, you immediately have a connection and something to discuss further. You may also learn something new from your new friend, giving them the opportunity to enlighten you, which makes them feel valuable.
9. What’s a typical day like for you?
This question can help you learn much more about how this new person than anything else they might tell you. How we actually spend our time and the actions we take says much more about us than our words do. It also lets you know whether or not this person has time for a real friendship.
10. What do you feel passionate about?
The most interesting people in the world are those who have a passion for something — or for many things. Does this person wake up enthusiastic and excited to begin their day? Do they have something amazing going on in their life? These are the people you want more of in your world.
11. What is the most out-of-character thing you’ve ever done?
We’ve all had our times of acting against our true selves — or maybe claiming our true selves after years of pretending to be someone else. These out-of-character times often occur with life transitions or major life events. How the person responded and what they learned from the experience can shed light on who they are.
12. How would the people closest to you describe you?
This is another opportunity to invite your new friend to share something positive about themselves — and maybe a few negative things as well. Sometimes self-deprecating humor comes out in these descriptions. Sometimes people feel uncomfortable sharing anything positive. Be prepared to answer this question about yourself as well.
13. If you could change one thing about your life, what would it be?
This question drills down to the core of our insecurities. What is it we don’t like about ourselves? This is a question for a second or third meeting, after you have some time with this new friend and know they aren’t offended by deep questions. Sharing insecurities and vulnerabilities deepens intimacy and trust in a friendship.
14. What age do you feel on the inside?
I love this question because invariably anyone over 40 feels much younger than they are. Sharing this phenomenon is a great way to recognize and acknowledge the essential person inside the body. We are all aging, but we aren’t our bodies. We are so much more, and we want our true friends to see us that way.
15. If you could only keep five possessions, what would they be and why?
This is a hard question for many people because we so identify with our possessions. It forces us to decipher our values in a nanosecond and define them through the few items we’d choose to keep. This question tells you what is most important to your new friend and whether or not you share similar values.
Having a list of good conversation starters in mind will help you initiate new connections that can lead to strong friendships. When you direct the conversation with these questions, you have a strategy for learning more authentic qualities of person standing in front of you and whether or not you share enough common interests and values to form a friendship.