As an introvert, it can be hard to connect with people. Finding new connections or even nurturing existing connections can feel exhausting at times. Yet many introverts desire a deep connection with others. Working through these conflicting feelings can be complicated and it’s unique to each individual. However, there are some tactics that can help all introverts foster more meaningful connections. Let’s explore…

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The introvert dilemma

Here’s an example of the conflicting dilemma that can occur if you are an introvert without enough close relationships (an example of my own internal monologue):

  • Me – “Man, I really wish I had a couple more close friends to hang out with.”
  • Spouse – “Do you want to go have dinner with so and so and her husband Saturday night? I think you’d really like him.
  • Me – “Uh, I don’t really feel like dinner. I’d rather stay home and relax Saturday.
Justin Winn sitting on white couch journaling

You see the conundrum here?

I definitely have the desire to have more close friends. However, taking the steps to cultivate and build new friendships is difficult. You can read more about my struggle to make new friends here.

Like most introverts, I hate small talk and struggle to start conversations. I don’t like staying on the surface level and chatting about the weather or politics. Instead, I want to dig in and hear about your latest adventure, new family challenge, goals and dreams – something a little more personal.

I’m working on it

Sometimes I think of topics for blog posts because they force me to be introspective and think of ways I can improve areas of weakness I have. This is one of those posts. Making new connections is something I really struggle with and I’m working on getting better at it. The tips below are for me just as much as you.

5 tips to form a deeper connection

So here they are, a handful of ways to help you (and me) foster the deeper connections we desire. As introverts, practicing some of these tips can be difficult but I’ve tried to make them as introvert friendly as possible.

1. Put yourself in a comfortable situation

Sometimes the hardest part is taking that initial first step. But know this, new friends and true connections don’t usually just fall into your lap. You need to seek them out. That means it’s on you to decide that you want to connect and reach out.

This is a hard one for me personally. I’m terrible at it. For guys, I think our masculinity gets in the way at times. I don’t know why it seems weird to ask another guy to grab lunch or a drink, because it shouldn’t. This is a weakness I recognize and am working on.

Man handing another man a postcard in a park

Putting yourself in a comfortable situation is helpful to kick start the two first steps of developing connections – Reaching out and getting together.

Reaching out

If you’re like me and struggle to just verbally ask someone to grab lunch, try and find a way to ask that is more comfortable:

  • Ask through written form (email or text)
  • Have someone else you know facilitate the meeting (wife, mutual friend, etc.)
  • Use social connections (LinkedIn, Facebook, etc.)

Getting together

It’s also important to find a comfortable setting to meet in. While most introverts have a general distaste for small talk and large social settings, they are usually more comfortable in one-on-one or small group settings.

I’ve found that being in a comfortable setting is helpful to make me feel comfortable and allows me to open up and connect. Some examples good settings:

  • Your favorite coffee shop
  • A restaurant you like
  • Your house
  • Any other mutual connection point you might have with the person (gym, sporting event, etc.)

2. Be present

When you make the effort to get together and form a connection, make sure you are all in and present. It’s impossible to create a deep connection with someone if your phone is buzzing on the table while they are talking. Make the effort to shut down internal and external distractions and make the most of your time.

Man and woman on street with cups looking at each other

Being present and in the moment is tough. As introverts, we tend to have a lot of “internal chatter” going on. We are thinking about 10 different things and silently observing 10 others. I’ve found the following tricks helpful for me to more present:

  • Arrive early to get settled in and comfortable.
  • Use a notepad to write down the thoughts, to-do’s. etc. that are in head before you meet. This helps to clear your mind and focus on the present.
  • Take a second to envision a positive experience. Think about what you’d like to learn about the person you’re meeting with.
  • Make eye contact. This might be uncomfortable at first – it’s ok.
  • Actively listen. Try and focus on hearing and taking in what the person is saying. Don’t let your mind wander to your next question or think about what you’ll say next.

3. Dig deeper

Introverts don’t like a lot of surface level small talk, so in order to make a deeper connection you’ll need to lead the conversation to more engaging topics. Luckily, this can be done by being curious and asking a few engaging questions. This will help you connect, as people are more open and feel socially closer to individuals who display curiosity.

For introverts, this is easier said than done. I am naturally curious, but sometimes in social settings I feel like my brain shuts down and I can’t think of a single question to ask. My mind races and all I can think of is “what should I say, what should I say?”. When nothing comes to mind, it can result in some really awkward silence.

Large question mark light on its side

This can be really frustrating. Especially when you leave the social setting and clear your head for a minute. Immediately, 3-4 good questions pop into mind that would have kept the conversation flowing smoothly. Sound familiar?

So how do you avoid this deer in the headlights trap?

You need to prepare. Think about (and write down) 2-3 questions you’d like to ask in advance to trigger deeper discussion and connection. Writing the questions down really helps you to remember them in the moment. Here are some tips:

  • Do your research – Use google, facebook, instagram, linkedin, etc. to learn more about them and find something you are interested in hearing more about. Did they recently take a trip? Are they active in a sport or activity? Did they live somewhere interesting? Do they have children?
  • Ask open ended questions – You want to trigger stories, not a simple yes or no. For example, “Tell me all about your trip to Thailand, what did you do?” is a better question than “I saw you just went to Thailand, was it fun?” Here are some open ended question examples.
  • Get personal and vulnerable – Using the points above, find a connection with the other person. Ask questions about that connection and be willing to share something vulnerable to let your guard down. Being humble and vulnerable can foster a quick connection and allow others to share deeper and more openly.

4. Play to your strengths

Introverts have particular strengths that come to us naturally. Play to these strengths to facilitate a deeper connection with others.

  • Listening – Introverts are used to sitting back and taking in information before responding. This makes us excellent listeners. Use this skill to ask meaningful follow-up questions during the conversation.
  • Observation – Introverts are good at observing others and their surroundings. Use the power of observation to read deeper into non-verbal cues like facial expressions and body language. These often tell us what a person is “feeling” vs. “saying”.
  • Intuition – Introverts also tend to read people well. This intuition allows us to develop a “gut feeling” about someone and what they represent and feel. While it’s not always perfect, if your gut feels a connection, lean into it. Use that intuition to overcome fear and open up.

5. Follow up

The final tip I have for connecting with people as an introvert is simple – follow up. I’ve found that the simple act of following up can a significant step towards building a connection. Not many people go above and beyond to check in after an initial connection, so when you do make that effort it really stands out.

thank you note on table with a pen next to it

If you seek a genuine connection, make sure you reach out with a thoughtful follow up. This can be in any form (letter/text/email). The key is to make your message personal and sincere. When I follow up with someone, I like to include the following:

  • A reference to a specific topic you discussed. This shows that you were listening and engaged.
  • An emotion. “I’m excited to learn more about your new business” is better than “You’re new business is interesting”.
  • A plan to get together again. It’s good to take ownership and set something up now. Throw out a few options to get together again and get a time on the calendar. If needed, follow up again to get a time set up!

What are your connection struggles?

Are you a thoughtful introvert that desires a genuine, deep connection with others? How do you overcome your natural tendencies and fears to make new connections? I’d love it if you shared in the comments so our community can hear about it.

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How to Connect with People, Even if You\'re an Introvert