What is it about trying to make new friends that can feel so intimidating? I mean, what do you even say to someone you’re interested in forming a friendship with? You don’t want to come on too strong, but you also don’t want your conversation to be entirely rooted in small talk.

Our pro tip for advancing the conversation and making someone feel like you’re interested and engaged? Ask a bunch of intentional questions.

How Asking Good Questions Improves Connections

Asking a question, followed by at least two follow-up questions, increases how much you’re
liked, according to a study published in the Journal of Personality and Social Psychology.

The key to connecting with others is being curious about the person while allowing them to feel heard and listened to, says Deborah Serani, PsyD, psychologist, author, and professor at Adelphi University. 

“Showing genuine interest in who they are, where they live, what they do, what uniqueness they possess gives the other person a sense of value socially,” she says. “The art of the conversation involves a reciprocal ebb and flow of this kind of interest—a back and forth of asking questions, listening to responses, and linking further conversations from these insights.” 

Friendly Questions To Ask a New Friend

Getting to know someone should have a bounce and lightness to the experience, “so, aim to learn more details about the other person’s work, family, interests, or hobbies,” says Serani.

Consider asking the following:

• What kind of work do you do?
• How long have you been in that field?    
• What did you do before you worked there?
• What town/city/neighborhood do you live in?
• How long have you lived there?
• Do you like living there?
• What made you move to this area?
• What do you like to do in your free time?
• Does your family live nearby?
• How many siblings do you have?
• Do you have children?
• How many children do you have?
• How old are your kids?
• Where did you grow up?
• Do you ever go back to your hometown? 

Questions About Things You Have in Common

When you’re in a situation that brings you together with others, like a party, club, or a child’s sporting event, it’s an opportunity to strike up a conversation. However, keeping it general is the best approach, says Diane Gottsman, etiquette expert and owner of The Protocol School of Texas. 

For instance, “at a cocktail party, too much information too fast is a red flag and asking personal questions sends the message you have difficulty reading social cues,” she says. 

When possible, ask open-ended questions that don’t instigate “yes” or “no” answers. This promotes follow-up conversation, adds Gottsman. 

Questions based on commonality that don’t sound nosy or intrusive might include: 

• How do you know the host?
• Do you know others at this party?
• Is this your first book club meeting?
• Have you volunteered at other places before?
• How long have you been singing?
• Do you have experience playing volleyball, or is this your first time playing?
• Which position does your daughter play?
• Is this your son’s first time on a swim team?
• Does your daughter play other instruments too? 

When Is It Time To Ask Deeper Questions?

Serani says deep subjects may not be best for first, second, or third social interactions because the intensity of deep questions requires a sense of safety, trust, and intimacy in a friendship. “It might feel like ‘too much’ during initial small talk, but as you get to know the other person, varying levels of exploring profound issues may become easier,” she says. 

Using non-question statements can help initiate deeper conversations. 

“Directional sentences can help show your interest, move the conversation along, and get another to share more about their life,” says Serani. She uses comments that start with “tell me,” “show me,” or “share how,” such as the following:

• Tell me about your time traveling abroad.
• Share how you met your partner. 
• Show me that restaurant you were talking about. 

Tips for Starting Conversations with Others

Before you enter a situation where you might meet new people, consider the following tips to help you engage in conversation. 

1. Engage Fully

Look at the person who is talking as you listen, and when you are talking, make eye contact too.

“Don’t be fiddling with your phone, checking out the scenery, leaning away, or appearing distracted. Be engaged, curious, and interested,” says Serani. 

2. Rephrase and Reflect

Let your new acquaintance know that you’re listening by reflecting back what you hear them share.

“Empathy and compassion are building blocks for forging good friendships,” says Serani. She suggests using statements like:

• Sounds like your work is very fulfilling.
• It’s stressful for you having four kids so close in age.
• Seems like you really enjoyed your weekend. 

3. Consider Your Talking Pace

The pace, tempo, and rhythm of how people engage in conversations is often overlooked, says Serani. When meeting someone new, she suggests being mindful of the tempo of your engagements.

For instance, she says shyer people require safety and comfort when talking, so conversations may take on a slower rhythm, while extroverts like banter and quickness, so they express an electric pace.

“Being able to adjust your social barometer to what others prefer, as well as monitoring your own social needs, can take some practice. The goal is to find a rhythm that works, and adjust the social pace as needed,” Serani says. 

4. Don’t Ask ‘Why’ Questions

“Why” questions can make a person feel defensive or criticized.

Instead, Serani says start with questions that use words like What, How and When. 

5. Avoid Controversial Topics

Avoid asking and answering questions related to politics, money, religion, sex, finances, or personal status. 

6. Don’t Talk Too Much About Yourself

After asking initial questions, Gottsman says to follow up with other questions that spin off the conversation.

“The key is to listen intentionally, without trying to bring the ball back to yourself,” she says. 

7. But Still Share Some Personal Information

So that it doesn’t seem like you’re bombarding the person with questions, Gottsman says share some personal information about yourself, “but think of a conversation like a tennis match; back and forth, back and forth.”